Kyle Norton is the Chief Revenue Officer at Owner.com, where he scaled revenue from $2M to $40M ARR in under 3 years while selling to one of the toughest markets: SMB restaurants. Before Owner, Kyle led sales at Shopify, where he helped architect one of the most operationally elite GTM orgs in SaaS.
Agenda:
00:00 – From Shopify to $40M ARR at Owner.com
06:40 – Why Founders Who Skip Sales Get Burned
11:50 – 90% Inbound, Then 70% Outbound — And Why Neither Is Enough
17:40 – How to Use AI in Sales to Massively Increase Outbound
24:30 – BDRs Don’t Get Paid for Demos. Only Closed Revenue.
30:50 – The 3-Part Sales Scorecard That Replaced My Gut
36:20 – I Posted a Job on LinkedIn and Got 1,200 Applicants
42:15 – I Fired a Rep on Day 11. Here’s Why.
49:40 – We Don’t Do Pipeline Reviews. The Secret...
55:00 – The One Call Close Script That Wins in 99% of Cases
1:03:10 – Why YouTube Is Our Underrated Growth Weapon
1:14:30 – Sales Is a Personal Development Exercise Disguised as a Career
1:20:45 – The Night We Closed Until 1AM and Hit the Number
Agenda:
00:00 – Why “Fund Returners” Are a Myth in Late-Stage VC
05:02 – Builder.ai Implodes: $500M Gone & Fraud Allegations Begin
11:40 – The Dirty Truth About Late-Stage Venture Math
15:57 – The Hinge IPO: Who Won, Who Lost, and Why It’s a Game Changer
23:03 – The Chime Bombshell: Late-Stage VCs Forced to Crystallize Huge Losses
27:14 – Why YC Is Both Chanel and Walmart—and Has Officially Won
33:41 – Seed Is Easy. Series A Is Brutal. Here's Why
39:50 – The Silent Killer: How Dilution Is Screwing VCs Without Them Realizing
46:04 – OpenAI’s $6B Jony Ive Deal: Genius or Delusion?
50:47 – Does OpenAI Win the Hardware War
1:02:09 – Duolingo, Klarna, and the Truth About AI Layoffs
1:13:10 – Only 20% of Unicorns Are Real. The Other 80%? Zombies
1:15:44 – Why 2021 Had an IPO Every Day — And Why That Won’t Return Soon
1:18:00 – Quickfire: AGI Dates, Half-Trillionaires, and Trump Tax Moves
Airwallex is the most insane story in startups:
Jack Zhang is the Co-Founder and CEO of Airwallex, one of the world’s fastest-growing global payments and financial infrastructure companies. Since founding the company in 2015, Jack has scaled Airwallex to over $130B in annual payment volume, $720M in ARR, and a global team of 1,800+ employees. Under his leadership, Airwallex has raised over $1.2BN from investors including Square Peg, Lone Pine, and Tencent.
In Today’s Episode We Discuss:
00:00 – The Best Angel Investment Ever: From $1M to $1BN
06:55 – From Lemon Factory and Petrol Station to Billionaire: The Early Days
15:20 – $5M side hustle while working full-time: how Jack did it
24:45 – Failing Three Times Before Product-Market-Fit
31:00 – The Term Sheet That Got Pulled and Lost Matrix $1BN
34:40 – Why We Rejected Stripe’s $1.2BN Acquisition Offer
49:05 – 0-$1B transaction volume in 9 months: How Shein Saved Airwallex
1:03:40 – We F****** Up Scaling internationally... & Burnt $200M/year
1:08:00 – When COVID hit, they lost 50% of revenue overnight
1:11:45 – Why Jack raised at 6x revenue and is now buying back stock himself
1:15:00 – The truth about secondaries and how much is “enough”
1:18:00 – The hiring mistakes that almost broke the culture
1:20:15 – Why Jack is Taking Out a Line of Debt for $70M
Luke Harries is Head of Growth at ElevenLabs, where he leads marketing, product, engineering, and developer experience. ElevenLabs has raised $281M with the latest round pricing the company at $3.3B valuation. Previously, Luke held roles at PostHog and Microsoft, and is also an angel investor supporting startups like Lovable and Runna.
In Today’s Episode We Discuss:
00:00 – The $3.3B Growth Engine Behind ElevenLabs
04:55 – Why Luke Said “No” to Investing in ElevenLabs (and Why He Was Wrong)
15:40 – How ElevenLabs Makes a Horizontal Product Strategy Work
20:15 – How to Build Sharded Growth Teams That Actually Scale
26:30 – The 7-Part Launch Playbook That Gets 700K+ Views Per Product
33:00 – The Truth About CAC, Payback, and Performance Marketing in AI
39:05 – SEO Isn’t Dead: The Mini-Tool Strategy You Should Steal
44:10 – Kill Your Inbound SDRs—The Case for Voice AI in Sales
48:40 – Why You Don’t Need PMs and the Rise of Growth-Led Product Teams
Agenda:
06:28 The Lopphole That Means Chime Has a Better Business than JP Morgan
10:51 Why Investors Who Invested at $25BN Will Make Money When it IPOs at $12BN
18:59 Are IPOs Dead & The Future of the Late Stage Private Market
27:32 Exits are Larger Than Ever: So What? What Happens? Who Wins? Who Loses?
40:51 Is Europe Totally F*******
43:48 Challenges of Going Public & What Needs to Change?
46:12 OpenAI's Future and Predictions
49:45 Rippling vs. Deel Lawsuit: Is Deel Screwed?
59:28 Why So Many Companies Are About To Become Database Companies
01:08:07 The Future of Salesforce: Buy or Sell?
01:13:28 Quickfire Round
Severin Hacker is the Co-Founder and CTO of Duolingo, the world’s most downloaded education app with over 100 million monthly users. Since its 2021 IPO, Duolingo has reached a market cap of $20BN. The company has raised over $183M from top-tier investors including CapitalG, Kleiner Perkins, Union Square Ventures, NEA, Ashton Kutcher, and Tim Ferriss. Severin is also an active angel investor, with standout bets including Decagon, one of the fastest-growing AI-native dev shops globally.
Items Mentioned In Today’s Episode:
00:00 – Why It's Harder to Raise $3M Than $100M
02:10 – The Real Reason Duolingo Couldn't Have Started in Europe
04:40 – Duolingo’s AI Pivot: What “AI-First” Actually Means
07:00 – The 12-Year Bottleneck Duolingo Crushed with AI
11:40 – How Duolingo Uses AI Internally (and Why They Love Cursor)
13:30 – Where AI Still Sucks (Especially in Engineering)
16:00 – Will AI Kill the CS Degree? Severin’s Surprising Take
18:00 – The End of Work? UBI, Purpose, and the Future of Labor
25:20 – OpenAI vs Duolingo: Are They Coming for Language Learning?
29:20 – Duolingo’s Biggest Mistake: “We Waited Too Long on This…”
39:30 – Duolingo’s Secret Sauce: What Investors Always Get Wrong
45:00 – Would You Go Public Today? Severin’s Surprising Answer
49:00 – Best and Worst Parts of Going Public—A Rare Honest Take
51:00 – Should Europe Give Up? Severin's Unfiltered Opinion
56:00 – Harsh Truth: “Europe Can’t Win Unless the U.S. Screws Up”
59:10 – Why Founders Have to Move to the US to Optimise Their Chance of Success
1:01:00 – Why Union Square Was the Only VC to Say Yes
1:03:00 – The Real Value of Tier 1 VCs (Even at Worse Terms)
1:05:00 – From PhD Student to Billionaire: Does Money Buy Happiness?
1:09:00 – Why Severin Sometimes Lies About His Job
1:10:20 – Founder Marriage Advice: “Write a Contract”
1:11:50 – How to Pick a Life Partner – Severin’s Tuesday Night Test
20VC: Duolingo Co-Founder on The Doomed Future of Europe, Reflections on Money, Marriage and the Future of AI
Yuhki Yamashita is the Chief Product Officer at Figma, where he leads the development of one of the world’s most beloved design platforms. Previously, he was Head of Product at Uber, overseeing the core rider experience used by millions globally. A master of product storytelling and team-building, Yuhki has redefined how world-class digital products are built and scaled.
Items Mentioned in Today’s Episode:
04:30 – "Simple is Lazy?" — Yuhki Challenges Product Dogma
07:45 – The Secret Behind Figma’s New Product Ideas (Hint: Users Hack It First)
09:00 – From Hack Week to Roadmap: How New Figma Products Are Born
10:00 – Are PRDs Dead? Yuhki's Spicy Take on the Death of Specs
12:30 – The ‘Screenshot Test’: Can Your Product Explain Itself in 1 Frame?
14:15 – Code Layers and ‘Living Designs’—This Demo Blew Everyone’s Mind
15:30 – Designers vs Coders: Who Really Owns the Future of Product?
17:45 – The Most Controversial Product Decision Inside Figma
19:00 – Why Figma’s Org Structure Could Kill the PM Role (For Real)
21:00 – Should Everyone Be a Designer and a Builder Now?
23:15 – Will Figma Have Fewer Engineers in 5 Years?
24:00 – Cursor, Windsurf & AI Coding Tools—What Figma Engineers Really Use
25:30 – AI’s Dual Power: Lowering the Floor, Raising the Ceiling
27:00 – Figma’s Biggest Product Flop? Yuhki Owns It
29:30 – The Magic of Product Storytelling—Even for Boring Compliance Tools
31:00 – Why Joy Must Be in the Product (and How Figma Bakes It In)
33:00 – Does Product Market Fit Even Mean Anything in 2025?
35:30 – Is Great Design Enough? Or Is It ALL About Distribution?
37:15 – Dylan’s Secret to Early Growth: Hacking Design Twitter
39:00 – Community Mistakes Startups Keep Making
41:00 – The One Thing Yuhki Wishes He Could Change at Figma
43:00 – Should They Have Launched 4 Products at Once? Time Will Tell
45:00 – When Do You Know a New Product Is Doomed?
46:30 – Why Designers Still Don’t Ship What They Design (and How to Fix It)
48:00 – From Uber to Figma: Yuhki’s Playbook for Massive Product Swings
53:00 – The Adobe Deal Breakup—How Figma Rallied
56:00 – What Yuhki Needs to Improve as a Leader (His Own Feedback Review)
58:00 – The Product Leader He Admires Most—and Why
59:30 – What Figma Still Gets Wrong About Product Culture
Please read the offering circular and related risks at invest.modemobile.com. This is a paid advertisement for Mode Mobile’s Regulation A+ Offering. Past performance is no guarantee of future results. Investing in private company securities is not suitable for all investors because it is highly speculative and involves a high degree of risk. It should only be considered a long-term investment. You must be prepared to withstand a total loss of your investment. Private company securities are also highly illiquid, and there is no guarantee that a market will develop for such securities. DealMaker Securities LLC, a registered broker-dealer, and member of FINRA | SIPC, located at 105 Maxess Road, Suite 124, Melville, NY 11747, is the Intermediary for this offering and is not an affiliate of or connected with the Issuer. Please check our background on FINRA's BrokerCheck.
Items Mentioned in Today’s Episode:
04:11 Owner’s New $120M Round at $1BN
06:05 Why Series A is F****** Today
14:55 Could Tiger Global Be Saved by OpenAI and Scale
22:43 Why SBF is the Greatest Investor of the Last Decade
31:34 Why No Individuals Should Invest in Venture Funds
36:27 Why Microsoft Laying 3% of Their Workforce Off is not Enough
41:38 OpenAI’s New CEO: Non-Technical CEOs Running OpenAI
44:48 Why Big Funds are Investing in Perplexity
54:43 Why Clay Should Raise a Warchest and Go to War
01:00:05 The Impact of AI on Marketing and Sales
Immad Akhund is the CEO of Mercury. Launched in 2019, Mercury has raised $500M in funding from Sequoia, Coatue, CRV, Andreessen Horowitz and others. He is a former part-time partner at Y Combinator and is an active angel investor, with more than 350 investments in startups including Rippling, AirTable, Rappi, Applied Intuition, and Substack.
In Today’s Episode We Discuss:
04:38 Exclusive News: New Fund Announcement
05:15 Lessons from 350 Angel Investments
12:27 Why Founders Should Always Push for the Highest Price
14:40 Biggest Wins and Misses in Angel Investing
22:56 How Sequoia Came to Lead the Series C for Mercury
31:32 Why Move From Angel to VC
33:41 Is It Wrong For Founders to Also Have Funds with LP Capital?
36:28 AI Investments: Overhyped or Worthwhile?
41:14 Raising a First Time Fund: Challenges & Surprises
49:47 The Future of Venture Capital
54:36 Quickfire Questions and Reflections
Eléonore Crespo is the Co-Founder and CEO @ Pigment, one of Europe’s fastest-growing companies. With Pigment, Eleonore has raised over $397M from the best in the world including ICONIQ, Greenoaks and IVP to name a few. Prior to Pigment, Eléonore was on the other side of the table as an investor with Index Ventures.
In Today's Episode We Discuss:
[04:10] “I had 3 surgeries. That’s when I knew I had to become a founder.”
[06:50] Why Index Ventures isn’t on her cap table
[08:40] Eleonore’s CIA-style co-founder hunt (she literally made a target list)
[11:50] Co-CEOs: “We talk 3x a day. That’s our superpower.”
[13:30] The boutique coffee metaphor for product excellence
[15:40] Yuri Milner’s 4 traits of legendary founders (one is shocking)
[17:30] “Hiring is everything. I hunt talent like a football scout.”
[19:00] Wild Olympic Games story → led to hiring a top CFO
[24:50] How she filters out title-chasers and political hires
[29:30] “Too much process? I make teams list the dumbest ones.”
[33:00] Her blunt answer on whether Europe can produce scale execs
[35:00] Why she raised so much money… even when they didn’t need it
[38:50] Board power is real: “They can fire you. I’ve seen it.”
[43:30] Rob Ward’s counter-cyclical advice: double down during a downturn
[44:50] “We closed a massive US deal… at 2am… while drenched in rain.”
[47:10] Selling into the US as a European founder—her full playbook
[50:20] The hardest part of being a CEO no one talks about
[54:00] “Children remind you what happiness is.”
[56:30] “I don’t fast. That would make me unhappy.” On longevity culture
[59:20] Why her husband knows nothing about Pigment
[01:04:20] “Forget $50B. I want to build a $200B company.”
LinkedIn: Eleonore Crespo
Pigment: pigment.com
Subscribe to 20VC for more conversations with the world’s best founders and investors.
Please read the offering circular and related risks at invest.modemobile.com
Today’s Topics:
04:44 Analysis of $3 Billion Windsurf Acquisition
12:39 Will Mega Funds Win the Future of Venture Capital
18:39 Does Every Fund Have to do Pre-Seed to Win Series A and B Today
27:53 Why AI Will Create Massive Unemployment
31:06 The $100,000 Bet on the Future of Work
35:52 Why Venture Has Become a Bundled Good
37:52 Why Stage Specific Firms Will Win: a16z vs Benchmark
40:16 What Does Harvard Losing It’s For Profit Status Mean for Venture
42:57 Why AI is Maiming and Not Killing Growth Companies on the Path to IPO
45:41 Decagon Raises 100x ARR: The Breakdown
52:50 Why VCs Are Upside Junkies and What That Means Today
01:03:37 Olo Looking to Sell: What Happens When Public Companies Want to Sell
Please read the offering circular and related risks at invest.modemobile.com
Bucky Moore is a Partner @ Lightspeed Venture Partners, announced exclusively in the show today on 20VC. Prior to Lightspeed, Bucky spent an incredibly successful 7 years at Kleiner Perkins working with Mamoon Hamid to build one of the most successful early stage firms of the last decade. Bucky has made investments in the likes of Prisma, Netlify, Browserbase and more.
In Today’s Episode We Discuss:
03:07 Big News: Joining Lightspeed Venture Partners
04:09 Why Mega Platforms Will Win the Next 10 Years of VC
09:33 Are Foundation Model Companies Good Venture Investments
16:04 What Applications Will Model Providers Buy/Build? What Will They Not?
22:03 How to Approach Price Sensitivity in a World of AI
28:25 Why is it BS to do Market Sizing When Making Investments in AI
34:03 Is the Future of VC Domain Specialization
38:38 How to Know What Company Wins in Super Competitive Markets
41:06 Why Every Firm Has to do Pre-Seed To Win in VC Today?
44:43 The Risks of Multi-Stage Investing: Is Signalling Risk Real?
48:53 Investing Lessons from Leading Rounds in Glean and Windsurf
56:54 Quick Fire Round: Lessons from Mamoon, Fave CEO, Next 10 Years
Reggie Marable is the Head of Global Sales at Sierra, a conversational AI platform for businesses. Sierra enables companies like ADT, Sonos, SiriusXM, and WeightWatchers to build AI agents that transform customer experiences. The company has rapidly become a hypergrowth leader in Silicon Valley, recently securing a funding round that values it at $4.5 billion. Before joining Sierra, Reggie was the Head of Sales in North America at Slack and the Area Vice President of Enterprise Sales at Salesforce.
In Today’s Episode We Discuss:
02:50 “What I Learned from Failing Early as a CRO”
06:06 The Most Effective Sales Strategy and the BS Sales Methodology
06:55 How to Build Sales Processes from Scratch
12:28 When and How to do Verticalised Sales Teams
14:15 How to Become World Class as Sales Prospecting and Outbound
17:21 How to Use Proof of Concepts to Win Enterprise Deals
22:04 Enterprise vs. Self-Serve: Both or One and How
30:09 Building a Sales Team from Scratch
37:39 Structuring the Hiring Process
41:14 How Founders F*** Up Hiring in Sales
46:25 Handling Salary and Title Expectations
51:36 How to Run Effective Deal Cycles
57:06:07 How to do Onboarding for New Sales Hires
59:07:48 How to do Post Mortems in Sales Processes
01:04:24 Negotiating Enterprise Deals
01:08:04 Quick Fire Round: Sales Tactics and Strategies
This episode is brought to you by Capchase, helping software and hardware companies close deals while accessing TCV upfront. Learn more at capchase.com/20vc.
In Today’s Episode We Discuss:
03:56 Why The Risk Lever Has Been Turned Higher than Ever in VC
06:04 Why IRR is the Hardest Thing to Control
09:36 Is Lack of Liquidity Short Term Temporary or Long Term Structural
12:17 Why Fund Returners Are Not Good Enough Anymore
16:03 Sequoia: The Best Strategy at the Worst Time
26:30 What it Takes to be Good at Series A and B Today
34:14 Only Three Company Types Survive AI
41:35 ServiceNow: 25% Pop, WTF Happened
45:29 Palantir and SAP Ripping: Do Incumbents Win AI
49:43 Are Benchmark Wrong to Invest in Chinese Made Manus
01:00:52 Geopolitical Risks in Investments
01:11:36 European vs. US Tech Culture