20VC: How To Build Meaningful Relationships With Your Investors, 4 Key Elements CEOs Must Focus On In Scale Mode & How Top Optimise Leadership Team Dynamics with Joel Flory, Founder & CEO @ VSCO

20VC: How To Build Meaningful Relationships With Your Investors, 4 Key Elements CEOs Must Focus On In Scale Mode & How Top Optimise Leadership Team Dynamics with Joel Flory, Founder & CEO @ VSCO

Joel Flory is the Founder & CEO @ VSCO, the startup that allows you to take your photography to the next level, with the mission to help everybody fall in love with their own creativity. To date, Joel has raised over $70m in funding with VSCO from some of the best in the business including Accel, Glynn Capital Management and Goldcrest Investments. Prior to founding VSCO, Joel founded his own photography company which he ran successfully for 10 years.

In Today's Episode You Will Learn:

1.) How Joel made his way from photographer to one of San Francisco's hottest startup founders today?

2.) How does Joel approach the current sentiment and approach to fundraising? Why were Joel and his co-founder unable to raise in the early days? How does Joel approach the element of investor selection? Brand name or partner? How does Joel look to really build relationships with VCs in compressed timeframes? What is Joel's litmus test to determine if a VC is interested? What single value add can a VC provide that is most important?

3.) What does Joel mean when he says, "you have to align your business model with your mission?" How can one really determine if they are aligned? How does this alignment change and alter with scale? What was the thinking behind the shift to a subscription business with VSCO? Was Joel worried it would impact the valuation and change the valuation mechanism to a multiple of revenue assessment?

4.) What do the optimal leadership team dynamics look like to Joel? What has worked well for Joel in binding the leadership team together? What have been some of the biggest challenges? How does Joel think about cross-functional communication across the leadership team?

5.) How does Joel think about his personal development today? Where would he like to improve? Where is he already strong? With a family and company in hyper-growth, how does Joel think about attaining that work-life balance? What advice would he have for other here? How does Joel determine what to say yes vs no to? What are some tips and hacks to this?

Items Mentioned In Today's Show:

Joel's Fave Book: How To Talk So Kids Will Listen and Listen So Kids Will Talk

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

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

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20VC: Figma's 250% Pop - The Greatest IPO Mispricing Ever | Meta and Microsoft Blowout Quarters: Broken Down | Cognition Raises at $15BN and Ramp at $22BN | CRV Downsizing and What It Means for LPs and GPs

20VC: Figma's 250% Pop - The Greatest IPO Mispricing Ever | Meta and Microsoft Blowout Quarters: Broken Down | Cognition Raises at $15BN and Ramp at $22BN | CRV Downsizing and What It Means for LPs and GPs

Agenda: 00:00 – The Worst IPO Mis-Pricing Ever: What Really Happened at Figma 02:30 – Fidelity vs Founders: How Important is Fidelity When Going Public 07:00 – Why Founders Secretly Want a Pop, Even If It Makes Them Look Stupid 10:15 – The Truth Behind the $3B Figma "Left on the Table" 14:00 – Direct Listings vs IPOs: Should Figma Have Gone Direct 23:00 – CEO Compensation is Broken, Brian Halligan Doesn't Hold Back 29:00 – The New Normal: Growth Rounds with Elon-Style Moonshot Packages 33:00 – Is Canva Next? Why Founders Should "Run, Forrest, Run" to the NASDAQ 36:00 – The Case for Going Public: VCs Are a Bigger Pain Than Public Markets 44:00 – Can AI Even Work for SMBs? Why No One's Cracked the Code (Yet) 51:00 – Meta's Monster Quarter: Growth, Cash Burn, and the Real AI Strategy 56:00 – CEO of the Year? Why Jensen Huang Leaves Zuck & Satya in the Dust 1:00:00 – Cognition's $15B Deal & Mass Layoffs: The Most Savage M&A Move of 2025 1:07:00 – Ramp's $22B Raise: Genius Move or Suicide Round? 1:09:00 – CRV Shrinks, Benchmark's Bet, and the Future of Venture Strategy

7 Elo 1h 20min

20Sales: $0-$3.7BN: The Databricks CRO's Playbook to Build the Fastest GTM Engine in SaaS History | How Databricks Beat Snowflake | How To Build a Sales Org of 5,000 and Close $190M Deals with Ron Gabrisko

20Sales: $0-$3.7BN: The Databricks CRO's Playbook to Build the Fastest GTM Engine in SaaS History | How Databricks Beat Snowflake | How To Build a Sales Org of 5,000 and Close $190M Deals with Ron Gabrisko

Ron Gabrisko is the Chief Revenue Officer at Databricks, where he joined in 2016. Under his leadership, Databricks has scaled from $0 to $3.7BN annualized revenue. He has grown the sales team from 0 to over 1,000 globally, leading expansion into enterprise, government, and international markets. Ron previously held senior sales roles at Cloudera and IBM, bringing deep experience in data and AI infrastructure. His tenure at Databricks has been defined by hypergrowth, multi-product adoption, and world-class GTM execution. Agenda for Today: 00:04 – The Databricks Origin Story: Ali, Ben Horowitz & 7 PhDs 00:08 – Ali vs JPMorgan: Turning Down $10M to Stay Cloud-First 00:13 – Prospecting Day: How Ron Scaled the GTM Culture 00:16 – Why Databricks' Pricing Model Was Its Secret Weapon 00:19 – Enterprise vs SMB: The Risky Bet That Paid Off 00:23 – From $2M to $13M ARR: How Ron Built the First Sales Engine 00:29 – Can AI Replace Salespeople? Ron's Brutally Honest Take 00:36 – How to Get Your First Million-Dollar Rep (and Keep Them) 00:42 – The Culture Secret Behind Scaling to 5,000 Sales Reps 00:45 – Why Databricks Waited Until $500M ARR to Go International 00:52 – What Makes a Great Sales Meeting? Ron's Gold Standard 00:58 – The Snowflake Wars: Why Ron Says Databricks Is 5 Years Ahead

4 Elo 1h 15min

20VC: Inside Carnegie Mellon's $4BN Endowment | Why 90% of LPs Shouldn't Invest in VC | The $140BN Problem with Multi-Stage Funds | The Hidden Math Behind DPI, TVPI, and Illiquidity with Miles Dieffenbach

20VC: Inside Carnegie Mellon's $4BN Endowment | Why 90% of LPs Shouldn't Invest in VC | The $140BN Problem with Multi-Stage Funds | The Hidden Math Behind DPI, TVPI, and Illiquidity with Miles Dieffenbach

Miles Dieffenbach is Managing Director of Investments at Carnegie Mellon University, where he helps oversee a $4 billion endowment with a focus on venture capital, private equity, and alternative investments. Under his leadership, CMU's private book has remained self-funding during some of the toughest years for liquidity. Agenda for Today: 00:04 – "I Had Cancer at 26 – It Changed Everything" 07:00 – Inside the $4BN Carnegie Mellon Endowment: The Investment Blueprint 10:45 – Are LPs Getting Screwed in Venture? 13:30 – 90% of LPs Shouldn't Be in Venture – Here's Why 16:00 – Seed Funds Are a Trap (And No One Wants to Admit It) 20:00 – The $140BN Problem with Multi-Stage Funds 24:00 – "Index Is the Best in the Game – Here's Why They Win" 29:30 – "The Dirty Secret of LPs: Brand Over Performance" 34:30 – "When Founder-Friendly Goes Too Far" 38:00 – "The OpenAI Bubble – Will It All Go to Zero?" 44:00 – "Ping Pong Diligence & Wildest Fundraising Stories"

4 Elo 1h 27min

20VC: Benchmark Loses Another Partner | Elad Gil Raises a Monster $1.5BN Solo GP Fund | Why Apple Need a Management Overhaul | Why Google is the Best Performing Hyperscaler | Will Cursor Hit $4BN ARR & Lovable $400M ARR by EOY 2026?

20VC: Benchmark Loses Another Partner | Elad Gil Raises a Monster $1.5BN Solo GP Fund | Why Apple Need a Management Overhaul | Why Google is the Best Performing Hyperscaler | Will Cursor Hit $4BN ARR & Lovable $400M ARR by EOY 2026?

Agenda: 00:00 - Why Benchmark Is Bleeding Partners (and Why That's the New Normal) 04:57 - "I Wouldn't Leave Benchmark… Unless I Had THIS" — Jason on Brand vs Autonomy 09:01 - The Rise of the Solo GP & The Death of LP Conventional Wisdom 13:50 - The Unstoppable Force of Elad Gil & The Myth of LP Discipline 18:45 - Is Vibe Coding the New SaaS? Jason's $10K/Month Spend Reveal 26:57 - Cursor's Growth Is Insane—But Is It Sustainable? 31:44 - Will Microsoft, Google, or Amazon Win the AI Infra War? 37:42 - Is GitHub Copilot the Biggest Miss in Microsoft's History? 44:15 - Are Big Tech Incumbents Now Too Powerful to Fail? 48:00 - Apple's AI Problem: Is It Time for a Management Overhaul? 52:30 - Figma's IPO: $30B Return, Zero Hype. What Happened? 1:06:00 - Final Bets: Cursor to $4B ARR, Lovable to $400M ARR, OpenAI to $800BN?

31 Heinä 1h 21min

20VC: a16z's Martin Casado on Anthropic vs OpenAI: Where Value Accrues | Cursor vs Replit vs Lovable: Who Wins and Who Loses | The One Sin in AI Investing | Why Open Source is a National Security Risk with China

20VC: a16z's Martin Casado on Anthropic vs OpenAI: Where Value Accrues | Cursor vs Replit vs Lovable: Who Wins and Who Loses | The One Sin in AI Investing | Why Open Source is a National Security Risk with China

Martin Casado is a General Partner @ a16z where he leads the firms $1.25BN infrastructure fund. At a16z, Martin has led investments in companies like Cursor, dbt Labs, and Fivetran to name a few. Before joining a16z, he co-founded Nicira, acquired by VMware for $1.26B. At VMware, he served as CTO of Networking. Widely regarded as a visionary in enterprise infrastructure, Martin has helped shape the modern cloud computing stack. Agenda: 00:00 – Analysis of Current AI Investment Landscape 04:45 – Will Anthropic Kill the AI App Layer? 09:20 – "The Oligopoly Is Coming—Just Like Cloud" 12:50 – Are AI Models Actually Terrible Venture Investments? 15:40 – Why it is BS to Put Down AI Apps for Having Temporary Revenue 21:30 – "Open Source Is a National Security Weapon—And We're Losing" 26:40 – "Have the Foundation Models of the Future All Been Founded Already" 34:30 – Why it is BS to Denigrate AI Apps for Having Low Margins 38:40 – Does AI Make 1x Engineers 10x or 10x Becomes 100x 44:10 – "We're All Dead Wrong About AI and Job Loss" 50:30 – "The Only Sin in Venture: Backing the Wrong Winner" 55:10 – What People Think They Know About Wealth But Do Not

28 Heinä 1h 10min

20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product

20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product

Fernando Fanton is one of the most respected product leaders in Europe, having held Chief Product Officer roles at Monzo and Just Eat. He previously led product and tech at Rappi, one of Latin America's most valuable startups. Today, Fernando is the CPO @ Property Finder; one of the biggest breakout unicorns from MENA. Agenda: 00:00 – Is "having a vision" actually killing great product teams? 03:15 – Why do most products suck—and what separates the great ones? 07:20 – Should we kill the PM role entirely? Fernando says maybe. 11:45 – Is Monzo's obsession with trust more powerful than speed? 16:10 – What's the #1 reason internal tools will never replace SaaS? 21:00 – Will AI wipe out the need for designers and PMs? 26:30 – Is it arrogant for product teams to protect users from "bad" choices? 32:15 – What's the future of product when OpenAI controls the whole stack? 37:40 – What Monzo product blew up—and why no one saw it coming? 42:55 – Can a bank built on principles really become a $100B company?

27 Heinä 1h 7min

20VC: Lovable Raises at $2BN & Hits $100M ARR | Is Cursor Worth $28BN at $1BN in ARR | How Do All Providers Deal with Anthropic Dependency Risk | Are Seed Funds F******: Have Mega Funds Won | Figma IPO Breakdown: Where Does it Price?

20VC: Lovable Raises at $2BN & Hits $100M ARR | Is Cursor Worth $28BN at $1BN in ARR | How Do All Providers Deal with Anthropic Dependency Risk | Are Seed Funds F******: Have Mega Funds Won | Figma IPO Breakdown: Where Does it Price?

Agenda: 00:00 – Did Jason Just Kill Replit? 03:45 – Why Claude Lies To You and Cannot Be Trusted 06:50 – You Cannot Trust Agents. Period. 10:20 – Why Windsurf Was Dead Without Claude 12:30 – Cursor vs. Lovable: What's the Better Bet? 14:40 – Should You Still Invest in Cursor at $28B? 18:05 – Would You Bet on Anthropic at $100B or OpenAI at $300B? 24:15 – Inside OpenAI's Secret Weapon: The Calvin French-Owen Memo 27:50 – Perplexity Just Crushed ChatGPT and Claude 32:15 – Will Cursor Build Their Own Models Before Anthropic Cuts Them Off? 33:20 – Figma's IPO at $16B: Outrageous or Fair Game? 41:55 – 90% of Seed Funds Are Cooked—Is Rob Go Right? 52:15 – How Often Do You Meet a Founder Who Can Return the Fund? 1:08:00 – Which Seed Fund Would You Back Today?

24 Heinä 1h 21min

20VC: Scaling to $1BN+ in Revenue with No Funding: Surge AI | The Most Insane Scaling Story in Tech |

20VC: Scaling to $1BN+ in Revenue with No Funding: Surge AI | The Most Insane Scaling Story in Tech |

Edwin Chen is the Founder and CEO of Surge. Founded in 2020, Surge has scaled to $1BN+ in revenue with zero external funding. At the same time, their competitor, Scale.ai raised over $1.3BN to reach $850M ARR. Today, Surge have the world's largest model providers as customers and have just 120 employees. Agenda: 00:00 — "Everyone Else Is Just a Body Shop" — Edwin Calls Out the Whole Industry 01:05 — Why 90% of Big Tech Is Wasting Time on Useless Problems 03:45 — "I Don't Do 1-on-1s" — How Surge Kills Meetings and Still Moves 10x Faster 05:55 — Will a Single Person Build a $1B Company? 08:10 — 100x Engineers Are Real — Here's How to Spot Them 12:10 — Why Most PhDs Are Useless in AI Training 14:20 — Built to a Billion With Zero VC — Edwin Explains How and Why 17:00 — "No Sales Team, No PR, No BS" — Why Surge Stays in the Shadows 21:15 — The Real Reason AGI Might Take Until 2040 24:45 — Will Synthetic Data Kill Human Labelling? 29:00 — "Academic Benchmarks Are a Scam" 31:05 — Why the Real Bottleneck in AI Isn't Compute or Models — It's THIS 33:00 — What Every AI Company Should Be Asking (But Isn't) 35:15 — "No, I Wouldn't Sell Surge for $100B" 39:00 — Is the Application Layer Doomed? Edwin Predicts the Future of AI Startups 46:30 — Have the Leading Foundation Models Already Been Founded? 48:10 — AGI Could Be Dangerous — And Most People Are Ignoring Why 20VC: Scaling to $1BN+ in Revenue with No Funding: Surge AI | The Most Insane Scaling Story in Tech |

21 Heinä 1h 6min

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