The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch – Details, episodes & analysis

AGENDA:

03:44 Rory Is So Old He Worked with Arthur Rock!!!

07:28 Goldman Sachs Acquires Industry Ventures for $665M

16:37 Thinking Machines Co-Founder Raises $2BN and Then Leaves for Meta

29:36 SoftBank Goes for $5BN Leverage Against ARM Stock To Buy More OpenAI

39:35 More Data Centres Than Offices: Are We In a Bubble

43:28 Where is the Alpha in Venture in 2025

51:48 What 90% of Managers Get Wrong About Portfolio Management

Mike Cannon-Brookes is the Co-Founder and Co-CEO of Atlassian, the $50BN software giant behind products like Jira, Confluence, and Trello. Since founding the company in 2002, he has scaled it to over 300,000 customers globally, generating more than $5BN in annual revenue. Atlassian now employs over 10,000 people across 13 countries and is one of the most successful bootstrapped-to-IPO stories in tech history. Mike is also a leading climate investor and co-owner of several major sports teams.

AGENDA: 

00:00 Why Unreasonable Men Win in Startups

07:22 How to Make Co-CEOs Work 

13:22 Are We in an AI Bubble? Is Everything Overvalued?

26:46 The Future of Software Development: More or Less Devs

32:53 Do Margins Matter in a World of AI

34:02 The Future of Vibe Coding…

36:35 Does Defensibility Exist in a World of AI

42:09 Is Per Seat Pricing Dead in a World of AI

49:01 The Founder Journey and Leadership

54:28 Quick Fire Round: Parenting Advice, Relationship to Money

Hemant Taneja is the CEO and leader of General Catalyst, the firm he has scaled over the last decade into one of the largest with over $40BN in AUM. He has been one of the most influential investors of the past two decades, leading early bets in Stripe, Snap, Gusto, Samsara, Grammarly, and Canva. He also played a pivotal role in Livongo's $18.5B merger with Teladoc, one of the largest digital health deals in history.

AGENDA: 

00:00 Introduction 

03:37 Is Hemant a CEO or an Investor?

05:42 With $40BN AUM Is General Catalyst Still a VC Firm?

12:11 Has Trump Done More to Hurt or Help the US?

13:25 No One is Talking About the True Impact of AI on Jobs

21:30 Is Hemant Concerned by the Concentration of Value in MAG 7? 

27:30 Has Trump Done More to Hurt or Help the US?

30:27 GC's Anthropic Investment: Upside from a $60BN Price 

37:06 Do Margins Matter in a World of AI

45:23 Does Revenue Growth Matter in a World of AI 

49:39 Why it is BS to Turn Down a Company Based on Price

56:06 We Have Invested $5BN Into Stripe Over 14 Rounds

01:00:02 VC is About To Be Flooded with Retail Investment: What Does It Mean for VC

01:08:51 "What I Learned Losing the Series A of Snap, Stripe, Samsara"

01:11:25 Future of Venture Capital: Walmart vs Chanel

Jonathan Ross is the Founder & CEO of Groq, the creator of the world's  first Language Processing Unit (LPUTM). Prior to Groq, Jonathan began  what became Google's Tensor Processing Unit (TPU) as a 20% project where he  designed and implemented the core elements of the first-generation TPU chip.  Jonathan next joined Google X's Rapid Eval Team, the initial stage of the famed  "Moonshots Factory", where he devised and incubated new Bets (Units) for Google's  parent company, Alphabet.

In Today's Episode We Discuss:

04:20 Interview with Jonathan Ross Begins

04:59 Scaling Laws and AI Model Training

06:22 Synthetic Data and Model Efficiency

12:01 Inference vs. Training Costs: Why NVIDIA Loses Inference

17:06 The Future of AI Inference: Efficiency and Cost

18:15 Chip Supply and Scaling Concerns

20:57 Energy Efficiency in AI Computation

25:40 Why Most Dollars Into Datacenters Will Be Lost

31:05 Meta, Google, and Microsoft's Data Center Investments

41:11 Distribution of Value in the AI Economy

42:10 Stages of Startup Success

43:17 The AI Investment Bubble

45:00 The Keynesian Beauty Contest in VC

48:40 NVIDIA's Role in the AI Ecosystem

53:39 China's AI Strategy and Global Implications

57:51 Europe's Potential in the AI Revolution

01:10:14 Future Predictions and AI's Impact on Society

Jason Pressman is a Managing Director @ Shasta Ventures who have made investments in the likes of Nest, Dollar Shave Club, Smule, Class Dojo and more. With 10 portfolio company investments under his belt, Jason invests in both enterprise and consumer, currently serving on the boards of Crittercism, subscription billing unicorn Zuora, as well as Nextdoor and mobile music platform Smule. Prior to joining Shasta, Jason was Vice President, Strategy and Operations at venture-backed Walmart.com, where he took the online retailer from zero to large scale revenue in five years.

In Today's Episode You Will Learn:

1.) How Jason made his way into the world of venture from Walmart? What were the big takeaways from seeing Walmart enter their hyper-growth phase?

2.) Why does Jason believe it is bullshit to say, "you never regret paying a high price for getting into a good company"? How does Jason evaluate entry point? What makes one entry point attractive and another not?

3.) What does Jason see as the catalysts for the opening of public markets to tech companies? How long does he think this will continue? Is he concerned by the likes of Yext, IPOing with less than aggressive growth rates?

4.) Why does Jason believe there are only 2 price points that work in SaaS? What are they? How does this affect the structure and operations of your SaaS startup? What are the circumstances in which these price points do not apply?

5.) Why does Jason believe that eSports will be bigger than the NBA in 5 years? What are the catalysts driving this change? What needs to be formulated within eSports for this to happen?

Items Mentioned In Today's Show:

Jason's Fave Book: First, Break All The Rules

Jason's Most Recent Investment: Plays.tv

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

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

WePay helps online platforms increase revenue through integrated payments processing, helping platforms offer ROI-positive integrated payments to their users - within their UX and without taking on fraud & regulatory exposure. WePay also offers award-winning support and can even work with your team thru Slack or Zendesk. Get the payments revenue you want, without getting bogged down every time a user has a payments question. Simply visit wepay.com/harry

PipeDrive is the Sales CRM and pipeline management software to use, with the primary view being the pipeline a clear visual interface that prompts you to take action, remain organized and stay in control of a complex sales process. This is why sales pros and deal makers love it (my words, not Pipedrive's). Plus it easily lets you find the stats you need and is fully customizable. Even better, you can signup for free on here it really is a must.

Kirsten Green is the Founding General Partner @ Forerunner Ventures, where she has raised over $250M from leading investors and has invested in more than 40 early-stage companies. Forerunner Ventures is the only VC firm to invest in both Dollar Shave Club and Jet.com, two of the biggest and highest-profile e-commerce exits in recent years, and counts Birchbox, Bonobos, Glossier, Hotel Tonight, Warby Parker and Zola among its portfolio companies. She's been honored in Time's 100 Most Influential People in 2017, named VC of the Year at TechCrunch's 2017 Crunchies Awards, and is part of Forbes 2017 Midas List.

In Today's Episode You Will Learn:

1.) How Kirsten came to found one of the most successful early stage funds of the past decade in Forerunner?

2.) Question from Michael Kim @ Cendana: How does Kirsten view the optimal portfolio construction theory for a thematically specialized consumer fund? What is the one question Kirsten asks herself pre-investing in a startup?

3.) Question from David Pakman @ Venrock: Given the scope of consumer as a space, is Forerunner large enough to attain the required ownership levels? What does this mean for the future of Forerunner in terms of further funds, opportunity funds and entry points?

4.) What are the 3 core principles to developing an exciting investment opportunity in the consumer space? What commonalities do they have? What do you look for in a consumer brand founder that might be different from a software founder?

5.) Why does Kirsten believe that Amazon has done more to make the market opportunity than they have to crush it? What makes Kirsten believe we really are in the early innings for commerce? How will we see the notion of brand evolve over the coming years?

Items Mentioned In Today's Show:

Kirsten's Fave Book: Charlie and The Chocolate Factory

Kirsten's Fave Blog: TheSkimm

Kirsten's Most Recent Investment: Packagd 

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

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

WePay helps online platforms increase revenue through integrated payments processing, helping platforms offer ROI-positive integrated payments to their users - within their UX and without taking on fraud & regulatory exposure. WePay also offers award-winning support and can even work with your team thru Slack or Zendesk. Get the payments revenue you want, without getting bogged down every time a user has a payments question. Simply visit wepay.com/harry

PipeDrive is the Sales CRM and pipeline management software to use, with the primary view being the pipeline a clear visual interface that prompts you to take action, remain organized and stay in control of a complex sales process. This is why sales pros and deal makers love it (my words, not Pipedrive's). Plus it easily lets you find the stats you need and is fully customizable. Even better, you can signup for free on here it really is a must.

Max Levchin is the Founder & CEO @ Affirm, the company that aims to remake consumer finance from the ground up. They have backing from some of the best in the business with over $400m in VC funding from the likes of Founders Fund, Lightspeed, Andreesen Horowitz, Khosla Ventures and Spark Capital just to name a few. Prior to Affirm, Max held numerous exec positions including Chairman of Yelp for 11 years and sitting on the board of directors @ Yahoo. Before that, Max founded Slide, subsequently bought by Google and was the Co-Founder & CTO @ Paypal.

In Today's Episode You Will Learn:

1.) How did Max come to co-found Paypal and how did that serve as the foundations for his founding of Affirm today?

2.) Why does Max believe there is a crucial misalignment between service providers and consumers in financial services? Does Max agree with Bill Clerico that 'we are still in the very early days for Fintech?'

3.) Having co-founded Paypal, Slide and now Affirm, how has Max changed as a leader and CEO? What does Max believe makes the truly great CEOs? Are there commonalities in how they operate and their skills?

4.) What does Max look for in all new hires or when evaluating founders for potential investment? Why is self-awareness so important for entrepreneurs to have? Why does Max want to be slightly terrified by how smart an individual is?

5.) How has having Children changed Max's perception of what is important and what he chooses to spend his time on? How does that reflect in his actions and self-discipline?

Items Mentioned In Today's Show:

Max's Fave Book: The Master and Margarita by Mikhail Bulgakov

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

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

eShares is the No 1 Cap Table Management platform, allowing for equity management, 409A valuations, and liquidity, all in one place. eShares is made for companies of all sizes with over 5,000 trusted customers including the likes of Squarespace, Kickstarter, and DoorDash just to name a few. To try out the must have service of the industry, simply head over to esharesinc.com it is a must.

Fond is the employee engagement suite with 3 core products, rewards: a recognition platform for rewarding achievements and milestones, perks: a premium corporate discounts program to show employees you care about them and then finally engagement IQ, a free employee engagement survey that allows you to measure the health of your organization. To check it out head over to fond.co

Roseanne Wincek is an investor with IVP, one of the leaders in growth financing with a portfolio including the likes of Snap, AppDynamics, SuperCell and Slack. At IVP, Roseanne focuses on investing in later-stage, high-growth consumer and enterprise companies, currently serving as a Board Observer for MasterClass and actively working with IVP's investments in Compass, Glossier, and Qubole. Prior to IVP, Roseanne was a Principal with Canaan Partners where she completed transactions for Beckon, Metacloud, and Stayful, just to name a few. Prior to VC, Roseanne was a co-founder @ imthemusic working to built music apps on the early Facebook platform.

In Today's Episode You Will Learn:

1.) How Roseanne made her way from science labs to startups and one of the valleys leading growth stage funds?

2.) Question from Maha Ibrahim @ Canaan Partners: How has the transition been from early to late stage? How do the industries differ in terms of startup visibility? Assessing the "what could be"? Allocation to reserve funding? Expected hold period?

3.)Why does Roseanne believe we are seeing a blurring of the lines between early and late stage? What is the effect for late stage of earlier stage funds having opportunity funds? What is the effect for early stage funds to see growth funds investing earlier??

4.) Why does Roseanne believe go to market strategy is now more important than ever? How serious does Roseanne believe the incumbency with regards to distribution channels is? Does this mean startups have to develop proprietary organic distribution channels?

5.) How does Roseanne view competition within the financing market? Question from Jenny Lefcourt @ Freestyle: How has Roseanne consistently gotten into some of the hottest most competitive deals?

Items Mentioned In Today's Show:

Roseanne's Fave Book: Einstein's Refrigerator: Tales of Hot & Cold

Roseanne's Most Recent Investment: Masterclass

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

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

eShares is the No 1 Cap Table Management platform, allowing for equity management, 409A valuations, and liquidity, all in one place. eShares is made for companies of all sizes with over 5,000 trusted customers including the likes of Squarespace, Kickstarter, and DoorDash just to name a few. To try out the must have service of the industry, simply head over to esharesinc.com it is a must.

Fond is the employee engagement suite with 3 core products, rewards: a recognition platform for rewarding achievements and milestones, perks: a premium corporate discounts program to show employees you care about them and then finally engagement IQ, a free employee engagement survey that allows you to measure the health of your organization. To check it out head over to fond.co

Mitch Lasky is a General Partner @ Benchmark, one of the world's leading VC funds with a portfolio including the likes of Twitter, Uber, Snapchat, eBay, WeWork, Yelp and many more revolutionary companies of the last decade. As for Mitch himself, Mitch has made investments or is on the boards of Snapchat, Riot Games, Discord, Outpost Games and Cyanogen, just to name a few. Prior to Benchmark, Mitch was CEO @ JAMDAT Mobile where he led the mobile gaming company from a 10 employee startup to a 700 employee global business leading their IPO on the NASDAQ in 2004 and later negotiating their sales to Electronic Arts for $680m.

In Today's Episode You Will Learn:

1.) How Mitch made his way from leading a 700 person gaming company to IPO to being General Partner with Benchmark?

2.) What does the investment decision-making process look like at Benchmark? Why does Mitch believe small is beautiful when it comes to VC teams? What is it that makes the Benchmark partnership the very special partnership it is?

3.) What makes Mitch say that "venture is very much like Hollywood? What does he mean by this? How does he apply this to talent evaluation? The hits-driven nature of the business?

4.) Why does Mitch struggle when analysing the future for VR? What is it about the current crop of innovation around VR that makes Mitch nervous? Where does Mitch see potential within the realms of VR & AR?

5.) How does Mitch view the continued rise of eSports? Does he believe that the industry will ever be as large as the traditional sports industry? What aspects of the industry does Mitch think is highly investable or not investable?

Items Mentioned In Today's Show:

Mitch's Fave Book: The Genius of System

Mitch's Fave Blog: Above The Crowd

Mitch's Most Recent Investment: Outpost Games

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

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

eShares is the No 1 Cap Table Management platform, allowing for equity management, 409A valuations, and liquidity, all in one place. eShares is made for companies of all sizes with over 5,000 trusted customers including the likes of Squarespace, Kickstarter, and DoorDash just to name a few. To try out the must have service of the industry, simply head over to esharesinc.com it is a must.

Fond is the employee engagement suite with 3 core products, rewards: a recognition platform for rewarding achievements and milestones, perks: a premium corporate discounts program to show employees you care about them and then finally engagement IQ, a free employee engagement survey that allows you to measure the health of your organization. To check it out head over to fond.co

Kim Scott is the Co-Founder @ Candor, the startup that allows you to become a better leader. Prior to founding Candor, Kim was a CEO coach at Dropbox, Qualtrics, Twitter and several other Silicon Valley companies. She was a member of the faculty at Apple University, developing the course "Managing at Apple," and before that spent 5 years at Google on AdSense, YouTube, and Doubleclick Online Sales and Operations at Google. Previously, Kim was the co-founder and CEO of Juice Software, a collaboration start-up.

In Today's Episode You Will Learn:

1.) How Kim came to founder Candor and be an advisor to Twitter, Qualtrics and Dropbox?

2.) How did Kim's interactions with Sheryl Sandberg while at Google shape how Kim views employee feedback? What is the most effective way for a superior to convey their feedback to their employee?

3.) What really is radical candor? How does it differ to more traditional "feedback"? What are the challenges of ruinous empathy? How does this play out in the work environment? How does this contrast to "obnoxious aggression"?

4.) Is this a gender issue? What makes it so difficult for people to be radically candid? Why is it a problem that people are told to 'be professional'? How does that act to de-humanize people?

5.) How do males go most wrong when conveying feedback to their female counterparts? Why is this a problem for both the males and the females involved? What can the female do to ensure that she is not disadvantaged by this?

Items Mentioned In Today's Show:

Kim's Fave Book: Anna Karenina by Leo Tolstoy

Kim's Fave Blog: Rands In Repose: Management

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

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

eShares is the No 1 Cap Table Management platform, allowing for equity management, 409A valuations, and liquidity, all in one place. eShares is made for companies of all sizes with over 5,000 trusted customers including the likes of Squarespace, Kickstarter, and DoorDash just to name a few. To try out the must have service of the industry, simply head over to esharesinc.com it is a must.

Fond is the employee engagement suite with 3 core products, rewards: a recognition platform for rewarding achievements and milestones, perks: a premium corporate discounts program to show employees you care about them and then finally engagement IQ, a free employee engagement survey that allows you to measure the health of your organization. To check it out head over to fond.co