20VC: The Twilio Memo: Bessemer's Byron Deeter on How a $125K Initial Check Became Bessemer's Largest Position, What The Influx of Late-Stage Capital Means For Venture Today & Why The Incumbent Advantage Is Now An Incumbent Disadvantage

20VC: The Twilio Memo: Bessemer's Byron Deeter on How a $125K Initial Check Became Bessemer's Largest Position, What The Influx of Late-Stage Capital Means For Venture Today & Why The Incumbent Advantage Is Now An Incumbent Disadvantage

Byron Deeter is a Partner @ Bessemer Venture Partners and one of the world's leading investors in SaaS and cloud. To date, nineteen of Byron's investments are valued above $1 billion, including ten IPOs and counting. Some of the incredible companies within Byron's portfolio include Twilio, ServiceTitan, Hashicorp, Canva, Intercom, DocuSign, SendGrid, the list goes on. Prior to joining the world of venture, Byron was an entrepreneur, raising a Series A from Bessemer and scaling the company to be one of the first global SaaS companies, reaching profitability and successfully selling to IBM.

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In Today's Episode with Byron Deeter You Will Learn:

1.) How Deven made his way into the world of venture and how that led to his becoming a Managing Director @ Insight, way back in 2000?

2.) The Market: Many people passed on Twilio, what did Byron see that others did not? Did Byron have concerns around the TAM? What made Byron feel comfortable they were not too early? How did Byron assess whether customers would churn off Twilio when they scaled to a size they could build their own infrastructure? How does Byron advise founders on this challenge today?

3.) The Team: What did Byron find some compelling about Jeff so early on? Jeff has been an incredible CEO from pre-seed to post-IPO, what has enabled Jeff specifically to scale with the company so successfully? What does Byron do to build the trust and rapport with founders that he does? What works? What does not work? How does that look today with Zoom?

4.) The Incumbents & Competition: Why does Byron believe the incumbent advantage is actually an incumbent disadvantage? What specifically has Byron found underwhelming about how the incumbents have tried to respond? In what tangible and specific way are startups better placed to win than incumbents? How does Byron advise founders to assess other startup competitors?

5.) The Funding: Twilio is Bessemer's single largest position ever, how does Byron know when is the right time to double down on an investment? What signals does he look for? Has this changed with the massive price inflation we have seen over the last year? How does Byron analyse the influx of new capital? Where is it good? What are the challenges to it?

Item's Mentioned In Today's Episode with Byron Deeter

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

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

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

24 Loka 1h 16min

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

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

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

23 Loka 1h 28min

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

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

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?

22 Loka 1h 15min

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

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

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

17 Loka 1h 13min

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

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

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

16 Loka 1h 19min

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

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

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

13 Loka 1h 3min

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

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

10 Loka 1h 2min

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

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

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

9 Loka 1h 24min

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