Episodes

20VC: Matt Mullenweg on Relationships to Risk, Money and Insecurity as a Leader | Lessons from a Parent's Passing and the Pre-Grieving Process | What is High Performance in Leadership Today?
July 11, 2022

20VC: Matt Mullenweg on Relationships to Risk, Money and Insecurity a…

is the Founder of Automattic, the force behind WordPress, Tumblr, WooCommerce, Jetpack, Longreads, Simplenote, Pocket Casts, and more. What started as a simple open-source blogging platform, Matt has turned into one of the most significant internet...

Listen to the Episode
20VC: How to Build Anti-Fragile Venture Portfolios Today | Why Diversification is Overrated in Portfolio Construction | How to Think Through Sizing Investments, Market Sizing and Pricing in Today's Environment with Mike Chalfen @ Chalfen Ve
July 8, 2022

20VC: How to Build Anti-Fragile Venture Portfolios Today | Why Divers…

is a solo GP with and one of the most respected and successful early-stage investors in Europe over the last two decades. Among Mike's incredible portfolio includes the likes of King.com (makers of Candy Crush), Houzz, Tipalti, Snyk, and Tray.io, to...

Listen to the Episode
20 Product: The Ultimate Guide to Product Reviews: What Makes the Best vs the Worst | How Often Should They Be | Who Should Be Invited | Who Sets The Agenda | How to do Follow-Ups Post Product Reviews
July 6, 2022

20 Product: The Ultimate Guide to Product Reviews: What Makes the Bes…

is an entrepreneur, master of product reviews, author, investor, and currently serves as Adobe’s Chief Product Officer and Executive Vice President, Creative Cloud. , often referred to as the father of the iPod is one of the leading product...

Listen to the Episode
20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early
July 1, 2022

20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Pr…

is the co-founder and CEO of , a leading HR technology company, currently valued at $5 billion. During the journey, Daniel has raised over $679M for Checkr from some of the best including , , Coatue, GV, and IVP to name a few. Prior to Checkr, Daniel...

Listen to the Episode
20VC: The Memo: Bill Gurley, Doug Leone, Keith Rabois; Investing Lessons from Prior Busts, How Their Investor Psychology Changed, What Can Be Applied To Today's Market
June 29, 2022

20VC: The Memo: Bill Gurley, Doug Leone, Keith Rabois; Investing Less…

is a General Partner @ , Bill, is widely recognized as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix, and Zillow.  is the Global Managing Partner @ , one of the...

Listen to the Episode
20VC: Accel's Sonali De Rycker on Building a Generational Defining Venture Firm; Hiring, Culture, Incentives | Investing; Biggest Mistakes, Biggest Lessons from Prior Crashes, Why Market Size is Dangerous to Focus On | Decision-Making; Type
June 27, 2022

20VC: Accel's Sonali De Rycker on Building a Generational Defining Ve…

is a Partner @ , one of the leading firms of the last 3 decades with a portfolio that includes the likes of UiPath, Miro, Spotify, and many more incredible companies. As for Sonali, Sonali led Accel’s investments in Avito (acquired by Naspers),...

Listen to the Episode
20VC: From Kitchen Table to $134M Fund II; Raising Your First Time Fund: Lessons from 400 LP Meetings, How To Find New LPs, What Materials to Use, How To Get LPs To Commit, The Challenges on Minimum Check Sizes and GP Commits and more with
June 24, 2022

20VC: From Kitchen Table to $134M Fund II; Raising Your First Time Fu…

is Managing Partner of , on a mission to change the face of entrepreneurship by investing in 1,000 diverse founders over the next 20 years. From a kitchen table with his Co-Founder, Jarrid, Henri has scaled Harlem in just a few years to their latest...

Listen to the Episode
20 Sales: Why Founders Should Not Be The One To Create The Sales Playbook, How To Structure Each Interview in the Hiring Process For Sales Reps, How To Use an "Interview Panel" Effectively and more with Zhenya Loginov, CRO @ Miro
June 22, 2022

20 Sales: Why Founders Should Not Be The One To Create The Sales Play…

is the CRO @ , the leading visual collaboration platform that helps bring teams together and meaningfully improves the way people work. At Miro, I run the go-to-market team of 700+ people across 11 global offices. Prior to Miro, Zhenya was the COO @...

Listen to the Episode
20VC: Gary Vaynerchuk on The Most Painful Lessons Learned but Why it was Good to Learn Them, Why You Have to Change the Timeframe You Have For Success, His Relationship to Money and How it Has Changed Over Time & His First 3 Angel Investmen
June 20, 2022

20VC: Gary Vaynerchuk on The Most Painful Lessons Learned but Why it …

is a serial entrepreneur and serves as the Chairman of ,  the CEO of  and the Creator & CEO of . Now Gary is a content machine and documents his life as a CEO daily through his social media channels which have more than 34...

Listen to the Episode
20VC: The Scaling Story of Soho House: Overcoming Dyslexia, Building a Global Brand, Scaling into The US, Retaining Exclusivity with Scale and The Journey to Going Public with Nick Jones, Founder & CEO @ Soho House
June 17, 2022

20VC: The Scaling Story of Soho House: Overcoming Dyslexia, Building …

is the Founder & CEO @ , it all started in 1995 when Nick opened the first location above his restaurant, Cafe Boheme, a members’ club for the local artists and actors of London. Today, Soho House is a global brand, a private members club that...

Listen to the Episode
20 Growth: Viral Loops; How To Create and Sustain Them, Why Interviews for Product and Growth Hires are BS and What To Do Instead, Mastering the Onboarding Process; Structuring the First 90 Days with Adam Fishman, Former Head of Growth @ Ly
June 15, 2022

20 Growth: Viral Loops; How To Create and Sustain Them, Why Interview…

is one of the leading growth practitioners of the last decade. Most recently, Adam was the Chief Product and Growth Offer at Imperfect Foods, where Adam built a 40-person product and growth organization, responsible for 70% of overall company metrics...

Listen to the Episode
20VC: Hubspot Co-Founder Dharmesh Shah on The 3 Risks All Startups Face, Angel Investing Rules; No Founder Meetings and No Due Diligence, SMB vs Enterprise; Lessons on Pricing, Distribution and Why You Should Resist Going Enterprise
June 13, 2022

20VC: Hubspot Co-Founder Dharmesh Shah on The 3 Risks All Startups Fa…

is the Founder and CTO @ , a full CRM platform with marketing, sales, service, and CMS software. Dharmesh started Hubspot in 2006 and today it is a publicly-traded company (NYSE: HUBS) with over 3,500+ people and a market capitalization of $16.9...

Listen to the Episode
20VC: Why and How Traditional Venture Firms Need to Innovate, Building Spreadsheets To Figure Out Relationships to Money, Ego and Identity Management with Success and The Biggest Lessons from Working with Mark Zuckerberg in the Early FB Day
June 10, 2022

20VC: Why and How Traditional Venture Firms Need to Innovate, Buildin…

is a Founder and Partner @ South Park Commons Fund, a home for the most talented technologists, builders, and domain experts figuring out what's next. Prior to SPC, Ruchi was the first female executive at Dropbox and served as their Vice President of...

Listen to the Episode
20 Product: Twitter's Former Head of Product, Kayvon Beykpour on How to Structure and Manage the Best Product Reviews, The Core Set of Questions to Ask All Potential Product Hires and When To Continue vs Quit on New Products
June 8, 2022

20 Product: Twitter's Former Head of Product, Kayvon Beykpour on How …

is one of the most prominent product leaders of the last decade. For the last 7 years, Kayvon has been at Twitter where he led all of the teams across Product, Engineering, Design, Research and Customer Service & Operations. Kayvon came to Twitter...

Listen to the Episode
20VC: Why DAOs Will Replace Venture Capital, What Existing Incumbent Venture Firms Can Do To Survive, The Biggest Challenges Facing New DAOs Today and Whether Web3 Will Bring More or Less Income Inequality
June 6, 2022

20VC: Why DAOs Will Replace Venture Capital, What Existing Incumbent …

is the Co-Founder of , a web3 startup that has raised over $28M from a16z, Kleiner Perkins, IDEO, and 300+ investors. Previously, Ian was Managing Partner of , a crypto venture fund backed by IDEO focused on web3, crypto, and...

Listen to the Episode
20VC: The Most Revealing Breakdown of Unit Economics for Quick Commerce; AOVs, Retention, Delivery Costs and more, Why The Business Model is Different for Emerging Markets & Will This Be a Market of Consolidation or Many Players
June 1, 2022

20VC: The Most Revealing Breakdown of Unit Economics for Quick Commer…

Over the last 10 days, we have seen unprecedented levels of layoffs from some of the biggest quick commerce providers in the world from Getir to GoPuff to Zapp and Gorillas. Today we dive into the world of quick commerce in emerging markets to uncover...

Listen to the Episode
20VC: Keith Rabois on Why Buy Low, Sell High Does Not Work in Venture, Keith's Biggest Lessons from Prior Crashes, Why Today's Public Markets are not an Over-Reaction, Why Valuation is a Trap & Why Wokeness is a Function of Entitlement
May 30, 2022

20VC: Keith Rabois on Why Buy Low, Sell High Does Not Work in Venture…

is a General Partner @ , one of the best performing funds of the last decade with a portfolio including Facebook, Airbnb, SpaceX, Stripe, Anduril, the list goes on. As for Keith, he has led the first institutional investments in DoorDash, Affirm and...

Listen to the Episode
20VC: Scaling from a $4M Angel Fund to $900M, Why Seed May Be The Best priced Asset Class and Not Overpriced At All & The 3 Stages of Fund Scaling and What it Takes To Build a Firm with Aydin Senkut, Founder and Managing Partner @ Felicis
May 27, 2022

20VC: Scaling from a $4M Angel Fund to $900M, Why Seed May Be The Bes…

is the Founder and Managing Partner of . An original super angel turned multi-stage investor, he has been named on the Forbes Midas List for the past nine years (2014-2022). Felicis has been an incredible 16-year journey starting with a $4M Fund I...

Listen to the Episode
20 Sales: How To Create and Execute a World-Class Sales Playbook, Why You Should Do Both PLG and Enterprise Sales at the Same Time, Three Non-Obvious Qualities the Best Sales Reps Have & The Four Steps To Sales Team Onboarding with Oliver J
May 25, 2022

20 Sales: How To Create and Execute a World-Class Sales Playbook, Why…

Oliver Jay (OJ) is one of the most successful sales leaders of the last decade. Most recently, OJ spent 6 years at Asana where he was hired as the company's first revenue leader. As CRO, OJ was responsible for product-led and sales-led revenue and...

Listen to the Episode
20VC: Oren Zeev on Raising 3 Funds and $1BN in 12 Months; Why Temporal Diversification is BS, Why Both LPs and GPs are Way Over-Diversified & Why Venture Partnerships are Sub-Optimal and Challenging
May 23, 2022

20VC: Oren Zeev on Raising 3 Funds and $1BN in 12 Months; Why Tempora…

is the Founding Partner @ and one of the OGs of solo capitalism. Oren has an incredible portfolio including investments in Audible, Houzz, Chegg, Riverside, Tipalti, TripActions, and Firebolt to name a few. Oren is also very unlike any other VC firm,...

Listen to the Episode
20VC: The Job of the CEO is Do As Little As Possible; How To Hire, What Questions To Ask, Why Pointy People are Always 100xers, How To Tell Great Stories Today & How Leaders Must Determine What To Delegate vs What To Control with Ian Siegel
May 20, 2022

20VC: The Job of the CEO is Do As Little As Possible; How To Hire, Wh…

is the Founder and CEO @ , a leading online employment marketplace that uses AI-driven matching technology to actively connect millions of businesses and job seekers to their next great opportunity. Since co-founding the company in 2010, more than...

Listen to the Episode
20Growth: Five Signs of Top Growth Talent and How to Detect Them, How to Structure and Conduct the Most Efficient Customer Discovery Process & The Framework to Determine Your North Star and When To Change it with Darius Contractor, Former V
May 18, 2022

20Growth: Five Signs of Top Growth Talent and How to Detect Them, How…

is one of the pre-eminent growth leaders of the last decade. As a growth OG, he has been VP Growth @ Airtable, where he led the growth, engineering, and product teams. Before Airtable, Darius was Head of Product Growth @ Facebook Messenger and...

Listen to the Episode
20VC: The Founding of General Catalyst, What it Takes to Build a Firm That Stands the Test of Time, Why VCs Need to Give Founders Greater Permission to Go For It & Why Venture Capital is Like Tennis with David Fialkow, Co-Founder @ General
May 16, 2022

20VC: The Founding of General Catalyst, What it Takes to Build a Firm…

is the Co-Founder and Managing Director @ , one of the leading venture firms of the last decade with a portfolio including Stripe, Snap, Airbnb, Anduril, Canva and many more amazing names. Prior to founding General Catalyst with Joel Cutler, David was...

Listen to the Episode
20 Product: iPhone Creator, Tony Fadell on Marketing Lessons Learned from Steve Jobs, What is Truly Great Product Marketing, How The Best Product Teams Do Post-Mortems and Product Reviews & Is Product Art or Science, Data or Gut?
May 11, 2022

20 Product: iPhone Creator, Tony Fadell on Marketing Lessons Learned …

, often referred to as the father of the iPod is one of the leading product thinkers of the last 30 years as one of the makers of some of the most game-changing products in society from the iPhone and iPod to more recently founding Nest, creating the...

Listen to the Episode