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Harry Stebbings

The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. 

If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show notes, resources and more.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Chris Olsen is the Founding Partner @ Drive Capital, the venture firm that believes the Midwest is the opportunity of our lifetime with more entrepreneurs building billion-dollar companies in the Midwest than in the last 50 years combined. Since inception in 2012, Drive have built an exceptional portfolio including the likes of Duolingo, FarmLogs, LeadPages and Udacity. As for Chris, prior to founding Drive he was a Partner @ Sequoia Capital on the West Coast where he learned the craft from some of the very best in the business. Before that he spent time at both TCV and UBS.
 
In Today's Episode You Will Learn:
 
1.) How Chris came to found the largest venture fund in the midwest, Drive, from being a Partner @ Sequoia Capital and learning the craft of venture there?
 
2.) Why does Chris believe that the biggest trend we will live through is the decentralisation away from Silicon Valley? What are the essential ingredients an ecosystem requires in order to foster this thriving tech hub? What does Chris believe it is fundamentally essential for companies to be in close proximity to?
 
3.) How does the lack of venture funds in the Midwest affect Chris' views on pricing? Would Chris agree with Peter Fenton, "never turn down a company based on valuation, it is a mental trap"? How does Chris look to differentiate between expensive and too expensive?
 
4.) How does Chris think about reserve allocation with Drive? What framework does Drive adopt to determine where to allocate reserve dollars? How does the shortage of follow-on investors in the midwest impact Chris' approach to follow on financing? What level does a company need to be in order to attract attention from larger growth funds?
 
Items Mentioned In Today's Show:
 
Chris' Fave Book: The Old Man and The Sea
 
Chris' Most Recent Investment: Duolingo
 
As always you can follow Harry, The Twenty Minute VC and Chris on Twitter here!
 
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
 
Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm. Simply head over to Cooley.com or you can check them out at Cooleygo.com.

20VC: The Biggest Trend Of Our Lifetime Is The Decentralisation of Entrepreneurship Away From The Valley, The Biggest Lessons From Learnings The Craft of VC at Sequoia & The Benchmarks Required to Attract Growth Investors with Chris Olsen, Founding Partne

David Cahn is a Partner at Sequoia Capital and one of the world's leading AI investors. At Sequoia David has led investments in Clay, Juicebox, Sesame, Kela, Stark, etc.. Before Sequoia, David was a General Partner @ Coatue where he led investments in Notion and Hugging Face. 
 
AGENDA: 
 
00:00 We Are in an AI Bubble
 
05:04 Why Building Physical Data Centres is a Moat
 
13:58 Winners and Losers in a World of AI
 
19:13 The Role of Big Tech and Monopolies
 
23:37 Breaking Down Circular Deals in AI: The Truth No One Sees?
 
38:19 Why Kingmaking is BS and VCs Do Not Make or Break Companies
 
41:30 The Importance of Margins in AI Investments
 
43:41 The Required Growth Rates in AI to Get Funded by Sequoia
 
45:30 The $0-$100M Revenue Club: Is Triple, Triple, Double, Double Dead? 
 
51:53 Why the Most Important Hire for Startups Today is 23 Year Olds
 
01:01:19 The Future of Defence: Who Wins and Who Loses
 
01:10:15 Quickfire: Biggest Miss, Parenting Advice, Doug Leone Advice

20VC: Sequoia's David Cahn on The Winners and Losers in AI | The $0-$100M Revenue Club: Is Triple, Triple, Double, Double Dead? | The Future of Defence: Who Wins and Who Loses | How to Analyse Margins and Growth Rates in a World of AI

Sandy Diao is one of the most exceptional growth leaders of the last decade. Sandy has scaled products to over 200M+ users and led growth teams at Descript, Meta and Pinterest. She is also a prolific writer all on things growth here. 
 
AGENDA: 
 
03:59 Biggest Growth Lessons from Pinterest
 
08:01 What is a Good vs a Bad Growth Hypothesis
 
11:11 Common Mistakes in Growth Strategies
 
14:57 Channel Fit: When You Have It & What To Do
 
25:43 Return on Ad Spend (ROAS) 101: How to Build a Paid Marketing Machine
 
30:08 How to Do SEO and Long-Term Growth Investments
 
33:22 Doubling Down on Successful Channels
 
36:31 The Unchanging Foundations of SEO
 
37:52 Generative AI Engines vs. Traditional Search Engines
 
41:12 Paid Marketing Channels: What's Overrated?
 
43:42 The Rise of User-Generated Content (UGC)
 
46:34 TikTok Ads: Expectations vs. Reality
 
49:55 Brand Marketing: What is Real vs What is BS?
 
53:33 The Importance of Feature Launches
 
01:01:50 Hiring for Growth: When and Who?
 
01:08:55 Quick Fire Round: Onboarding, Notifications, and Growth Channels

20Growth: How to Build a Paid Marketing Machine: ROAS (Return on Ad Spend) 101 | The Rise of User Generared Content and How to Use It | TikTok Ads: Expectations vs. Reality | Hiring for Growth: When and Who with Sandy Diao

AGENDA:
 
04:50 Benchmark's New Partner: Everett Randall
 
10:19 Revolut Raises $3BN at a $75BN Valuation: Another Loss for Public Markets?
 
28:39 Why Today is as Bad as the Hype of COVID in 2021
 
32:10 Why Vertical SaaS is a Bad VC Investment Today
 
36:14 Why Everyone Investing in Legal SaaS Will Lose Money
 
44:16 Why King Making is More Real Than Ever
 
55:23 Why Your Smallest Customers Need to Pay $10K Minimum
 
01:01:37 Why VC is a S*** Asset Class
 
01:09:29 Why Today is Harder Than It Has Ever Been in VC
 
01:25:18 Closing Thoughts and Reflections

20VC: Why VC Today is Worse Than 2021 | Why Vertical SaaS is a Bad Investment Today | Why We Are Deluding Ourselves on Growth Expectations | Revolut Raises $3BN at a $75BN Valuation | Benchmark Adds Their Newest General Partner

Alex Bouaziz is the Co-Founder and CEO @ Deel, the $17BN global payroll juggernaut that just last week announced their latest $300M fundraise led by Ribbit, a16z and Coatue. Deel has been on the most insane journey, they do $1BN+ in ARR, they just had their first $100M revenue month and they have been profitable for over 3 years. 
 
AGENDA:
 
03:38 Announcing $300M Fundraise at a $17BN Valuation
 
06:24 Rippling vs Deel: WTF is Going On? Where is the Lawsuit? 
 
14:01 Why 1-1s Are BS and Leaders Should Stop Doing Them
 
17:31 Do Rich Leaders Make Better Leaders
 
28:33 Biggest Lesson from Ben Horowitz? Why Most CMOs Are Bad?
 
34:48 Lessons from Nik @ Revolut and Why Companies Need to Make Their Own Software
 
42:23 Deel's Acquisition Playbook: Lessons from 13 Acquisitions
 
45:17 How to Price Acquisitions? How to Align Incentives with Founders?
 
55:45 Deel is Profitable and Growing Fast: When is the IPO?
 
01:01:35 Best Acquisition Ever + Worst Ever: What Did We Learn?

20VC: Deel CEO Alex Bouaziz on Raising $300M+ at a $17BN Valuation | Deel vs Rippling: WTF is Going On | Management Lessons from Ben Horowitz and Nik Storonsky | Deel's M&A Playbook: Lessons from 13 Acquisitions: What Works & What Doesn't

Zach Lloyd is the Founder and CEO of Warp, the next-generation developer terminal reinventing how engineers build and collaborate. Warp has raised over $70M from top-tier investors including Sequoia Capital, GV, Dylan Field, and Elad Gil. Before founding Warp, Zach was Principal Engineer at Google, where he led development of Google Docs, and later served as CTO at Time. He's one of the most respected engineering minds redefining the future of developer tools.
 
AGENDA: 
 
04:14 Biggest Product Lessons from Rewriting Google Sheets
 
07:10 Why I Would Short Google: Leadership and AI Strategy
 
09:55 Comparing AI Models: GPT, Claude, and Gemini: Who Wins and Loses
 
17:04 Do Margins Matter in AI?
 
24:57 Adding $1M in ARR Every Week: Is Triple, Triple, Double, Double Dead?
 
33:58 How to Build Defensibility in a World of AI?
 
43:05 OpenAI vs Anthropic: Who Wins and Why?
 
44:25 Biggest Fundraising Lessons Raising from Sequoia, Elad Gil and GV
 
50:56 Why Sequoia are the Best VC
 
53:51 What Every Founder Gets Wrong in Fundraising
 
01:01:30 Quick Fire Questions and Final Thoughts

20VC: The Startup Adding $1M ARR Every Week | Competing Against OpenAI's Codex and Claude Code: Who Wins | Why Gemini is Failing and GPT-5 Is Winning | Do Margins Matter in a World of AI | The Ugly Truth About AI Coding with Zach Lloyd, Warp

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

20VC: $3.5BN - The Price Zuck Paid for Thinking Machines Co-Founder | Goldman Sachs Acquires Industry Ventures for $665M | Softbank Borrows $5BN Against ARM Holding to Invest More Into OpenAI

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

20VC: Atlassian CEO on Why Everything is Overvalued & Are We in an AI Bubble | Do Margins Matter & Does Defensibility Exist in an AI World | Is Per Seat Pricing Dead & The Future of Vibe Coding with Mike Cannon-Brookes

Chris Degnan is the former Chief Revenue Officer at Snowflake, where he was instrumental in scaling the company from less than $1M in ARR to over $3B in annual revenue. He joined as the first sales hires and built Snowflake's go-to-market engine from scratch, growing the team from to more than 6,000 globally. Under his leadership, Snowflake became one of the fastest-growing enterprise software companies in history, achieving a record-breaking IPO in 2020.
 
AGENDA:
 04:34 How to Build a Sales Team from Scratch 07:49 How to Hire and Evaluate Sales Leaders 15:23 Four Big Lessons Scaling Snowflake to $3BN ARR 31:30 Comparing Snowflake and Databricks: What Databricks Did Better? 35:26 How to Manage Sales Team Morale in Competitive Markets 43:53 Why Customer Success is BS and What To Do With It 48:31 How Every Sales Leader Needs to Change in An AI World 49:37 Biggest Reflections on Sales Leadership 54:38 Quick Fire Questions and Final Thoughts 20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan

20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan

AGENDA: 
 
03:29 OpenAI and AMD's Major Partnership
 
07:35 Microsoft Have F***** Up the OpenAI Partnership 
 
17:08 OpenAI's Developer Day Announcements
 
20:45 Why VC is the Most Forgiving Asset Class on Price and Valuation
 
29:10 What Does it Take to IPO in 2025: Why Snyk Will Not IPO
 
42:30 Four Strategies Companies Need to Take to Own Their Own Destiny
 
49:31 Vercel Raises $300M at $9BN: Suicide Round or Strategic
 
55:39 Does King Making Really Work in Venture Capital: Legora vs Harvey
 
01:08:11 Chamath Raises Latest SPAC: SPACs are Back
 
01:10:56 Polymarket Raises $2BN at a $9BN Valuation
 
01:14:53 Quick Fire Questions and Wrap-Up

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

Amit Bendov is Co-Founder & CEO of Gong, the leading AI-sales platform. The company has raised over $600 million from some of the best in the world including Sequoia, Thrive, Salesforce and more. Gong has surpassed $300M in ARR, serves thousands of customers (including multiple Fortune 10s), and is valued at over $7BN. 
 
AGENDA: 
 
00:00 – Why CRM Was Always a Lie and Gong's Secret Insight
 
04:30 – Will AI Kill Salesforce? Mark Benioff's Nightmare
 
08:15 – Why 99% of VCs Said No to Gong's Seed Round
 
12:00 – The Shocking Trial Close That Changed Everything
 
18:00 – Can AI Make Every Seller Perform Like LeBron?
 
20:30 – Will Sales Software Shift from Software Budget to Human Labor Budget?
 
25:00 – Why AI SDRs Are "Stupid" and Bound to Fail
 
35:00 – Gong's Darkest Hour: Shrinking, Churn, and Losing Muscle
 
41:30 – The Re-Acceleration Playbook: How Gong Got Back to Hypergrowth
 
54:00 – Would Amit Ever Sell Gong—or Take It Public?

The Twenty Minute VC

20VC: Why AI SDRs are BS and Do Not Work | How to Use AI in Your Sales Team and Process to Win Today | What Skills Do All New Reps Need to Have in an AI First World with Amit Bendov, CEO @ Gong

20VC: Why AI SDRs are BS and Do Not Work | How to Use AI in Your Sales Team and Process to Win Today | What Skills Do All New Reps Need to Have in an AI First World with Amit Bendov, CEO @ Gong

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