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

By Harry Stebbings

Tech News Business Investing

What's The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch about?

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.

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20Product: When to Hire a C...

02.03.2023

Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. Before Calendly, Annie led Glassdoor’s product vision and user experience, managing a 70-person product and design org. Shreyas Doshi is an investor, advisor, and ...

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

02.03.2023 20Product: When to Hire a CPO, The Three Different Types of CPO, How To Know What You Need, How To Structure the Hiring Process, What Are the Must-Ask Questions, What Tests and Case Studies Should Be Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. Before Calendly, Annie led Glassdoor’s product vision and user experience, managing a 70-person product and design org. Shreyas Doshi is an investor, advisor, and ...
02.01.2023 20VC: From $57M in ARR to $297M in Just 12 Months; Why Speed of Execution is the Most Important Factor to Success, Hiring 2,000 People in 3 Years Remotely & Secondaries; Why, When and How Much To Take Alex Bouaziz is the Co-Founder and CEO @ Deel, the all-in-one platform made to simplify all things HR, built for global teams near and far. In the last year alone, Alex has scaled Deel from $57M in ARR to $295M, ...
01.30.2023 20VC: Homebrew's Hunter Walk and Satya Patel on Why $100M is Not Enough To Execute a Seed Strategy Today \| Why They Decided not to Raise New External Funds \| Where Are We in the Cycle & What is Truly Hunter Walk and Satya Patel are Co-Founders and Partners @ Homebrew, one of the leading seed funds of the last decade. Following 10 years of stellar returns with investments in the likes of Chime, Plaid, Gusto and many others, they ...
01.27.2023 20VC: Canva Co-Founder, Cliff Obrecht on The Journey From 100 VC Rejections to a $40BN Company, Why Good Enough is Not Good Enough, The Secret to Hiring Non-Obvious Talent and Relationships to Money a Cliff Obrecht is the Co-Founder & COO @ Canva, the free-to-use online graphic design tool that makes it easy for anyone to design anything from presentations to videos and social media. Cliff and Mel have scaled Canva to over 60 ...
01.25.2023 20Sales: Why You Should Not Do PLG and Enterprise Sales at the Same Time \| How To Move Into Enterprise Sales Gradually \| How To Make a Comp Plan For Sales Teams \| Why Discounting is Good and Can Be Us Stevie Case is the CRO @ Vanta where she oversees Vanta’s go-to-market team to support the company’s rapid growth. Prior to joining Vanta, Stevie was Vice President of Mid-Market Sales at Twilio, joining as one of their first account executives, ...
01.23.2023 20VC: USV's Albert Wenger on What Elon Musk Should Do with Twitter \| The State of Crypto Today; The Impact of SBF and Why Now is the Best Time To Invest in Crypto \| Are We Too Late to Save The Climate Albert Wenger is a managing partner at Union Square Ventures, one of the most successful venture firms of the last decade with a portfolio including Coinbase, Twitter, Twilio, Etsy, and many more. Before joining USV, Albert was the president of ...
01.20.2023 20VC: Turning Canned Water into a $700M Media and Health Company, What Makes Truly Great Brands, How Founders Can Build Their Brand From Day 1 Today & How to Create Viral Content with Little to No Bud Mike Cessario is the Founder and CEO @ Liquid Death, the man hacking the healthy beverage market with the first hilarious water brand. It is working, Liquid Death's latest valuation was over a staggering $700M and Mike has raised over ...
01.18.2023 20Growth: When To Make Your First Growth Hire? How To Structure the Hiring Process for Growth? Five Core Things the Best Growth Hires Do in the First Week? What to Expect New Growth Hires to Achieve i Hila Qu is one of the leading growth execs of the last decade. Hila helped scale Acorns from 1 million to 5 million users as their VP of growth. Hila then joined GitLab, where she launched their PLG motion (on ...
01.16.2023 20VC: a16z's Jeff Jordan on The Ultimate Guide to Investing in Marketplaces, Two Core Features to Look for in All Marketplace Investments, Why Fragmented Supply is so Important & Lessons from Airbnb, Jeff Jordan is a General Partner @ a16z where he serves on the boards of Airbnb, Incredible Health, Instacart, Lookout, and Pinterest, just to name a few. Before a16z, Jeff was CEO OpenTable, where he led the company during a ...
01.13.2023 20VC: WTF is Going On in VC? Are VCs Still Investing? How Has What VCs Want in Investments Changed? Are LPs Investing in New Funds? Why VCs That Invest in Public Markets Are Losers? Dec 2023; Will It The question is: "are VCs still investing?". Today we are joined by Jason Lemkin; one of the OGs of SaaS of the last decade. As the Founder of SaaStr, he has inspired more SaaS founders than one can imagine building ...
01.11.2023 20VC: The Memo: How to Raise a Venture Capital Fund (Part I) \| The Core Lessons from Raising $400M Over The Last Four Years\| The Biggest Mistakes VCs Make When Fundraising \| How To Find and Build Rela How To Raise a Venture Capital Fund Over the last 4 years, I have raised around $400M across different vehicles from many different types of investors. Today I am going to break down the early stages of how to raise ...
01.09.2023 20VC: From a $5,000 College Fund to a $10BN+ Public Company, How to Beat People Who Are Smarter Than You, Why Happier Teams Outperform and How Software Buying Patterns are Changing in 2023 with Henry Henry Schuck is the Founder and CEO @ ZoomInfo. From ZoomInfo's founding moment, putting $25,000 on a credit card, Henry has led the company to today, with over $1BN in ARR, a market cap of over $10BN, and a team ...
01.06.2023 20VC: Why Financial Planning and Goals Do Not Work, The Decision to Ban Politics in the Workplace and Losing 1/3 of the Team Overnight & The One Question That Will Drive All Decision-Making for Leader Jason Fried the Co-Founder and CEO at 37signals, makers of Basecamp and HEY. Over an incredible 21-year journey, Jason and his co-founder David have scaled Basecamp to become the communication tool trusted by millions. Jason is also the co-author of ...
12.21.2022 20VC Special: How To Fundraise Like a Pro: How to Size and Price a Round, How to Create FOMO and Urgency in a Fundraise, How to Structure Angel Allocations, The 7 Deadly Sins of Fundraising Decks, The 20VC: Fundraising 101 Today we are going to walk through the process of raising a funding round for a hypothetical company. We will break it down by different stages in the fundraising process and at those stages I will talk ...
12.19.2022 20VC: Peloton CEO Barry McCarthy on Leadership Lessons Learned from Reed Hastings and Daniel Ek, What is Peloton's Competitive Advantage and Why Peloton is a Team and Not a Family Barry McCarthy is Peloton’s CEO and President. McCarthy is a seasoned executive who served as CFO of Spotify from 2015 to January 2020, and CFO of Netflix from 1999 to 2010. Prior to Netflix, McCarthy held various leadership positions in ...
12.16.2022 20VC: Leadership Lessons from Bill Gates and Steve Ballmer, The Early Days of TheFacebook Advising Mark Zuckerberg and Why Now is Not the Right Time For Startups to Stockpile Cash with Hadi Partovi, C Hadi Partovi is a tech entrepreneur and investor, and CEO of the education nonprofit Code.org. Before founding Code.org, Hadi founded two prior startups: Tellme Networks (acquired by Microsoft, discussed on 20VC with Emil Michael), and iLike (acquired by Newscorp). Hadi ...
12.14.2022 20 Sales: Webflow's Maggie Hott on When to Start and How to Scale the Best Outbound Sales Team, Why Founders Should Not Hire a Head of Sales First, The Must Ask Questions When Hiring Sales Reps and Ho Maggie Hott is the Director of Sales @ Webflow where she leads their Sales Dev, Account Executive, and Solution Engineering orgs. Prior to Webflow, Maggie spent an incredible 6 years at Slack in a period of hypergrowth for the company ...
12.12.2022 20VC: Mailchimp's Ben Chestnut on The Biggest Leadership Lessons Scaling to a $12Bn Acquisition and $1BN+ ARR, The Secret to Happiness, Being a Great Husband and Father & Why 2021 was the Right Time T Ben Chestnut is the Co-Founder of Mailchimp, the all-in-one marketing platform for small businesses. Last year, in Sept 2021 it was announced that Intuit would acquire Mailchimp for a reported $12BN. There are so many things to love about the ...
12.09.2022 20VC: The Story of Turning Around MTV, AOL and Time Warner \| How To Be Effective When Making Hard Decisions \| Tactics vs Strategy and Why Plans Are BS with Bob Pittman, CEO @ iHeartMedia Bob Pittman is Chairman and CEO of iHeartMedia, Inc., the number one audio company in America. Prior to iHeart, Bob has just had the most amazing career as a co-founder and programmer who led the team that created MTV. He ...
12.07.2022 20 Product: Marty Cagan on The Four Questions of Great Product Management, Product Lessons from Marc Andreessen, Ben Horowitz and eBay's Pierre Omidyar & The Difference Between Truly Great Product Tea Marty Cagan is one of the OGs of Product and Product Management as the Founder of Silicon Valley Product Group. Before founding SVPG, Marty served as an executive responsible for defining and building products for some of the most successful ...
12.05.2022 20VC: a16z's Martin Casado on How the Venture Model is Broken, Why VCs Should Be Running Wall St, Who Wins and Who Loses in the Next Generation of Venture & Investing Lessons from Marc Andreesen, Ben Martin Casado is a General Partner @ a16z where he focuses on enterprise investing. At a16z, Martin has led investments and serves on the board of dbt Labs, Fivetran, Material Security, Ambient AI and many more incredible companies. Before venture, ...
12.02.2022 20VC: Plaid and Column Co-Founder, William Hockey on Why the Brands that Win in Fintech Will Not Be Financial Services Brands, What US Banking Can Learn from China & Why Companies Can Be Built Slower Will Hockey is the Co-Founder and Co-CEO @ Column, the only nationally chartered bank built to enable developers and builders to create new financial products. Before co-founding Column, Will was the Co-Founder, President, and CTO @ Plaid, a world-leading data ...
11.30.2022 20VC: Jason Lemkin on Why Founders Do Not Care About Their VCs Anymore, Why Zoom Made Us All Worse Investors, Why 80-90% IRR Should Have Been Warning Signs and the Algolia Journey From Seed to $2.25BN Jason Lemkin is one of the OGs of SaaS of the last decade. As the Founder of SaaStr, he has inspired more SaaS founders than one can imagine building "The World’s Largest Community for Business Software." Jason also invests out ...
11.28.2022 20VC: Wolt CEO, Miki Kuusi on Leadership Lessons Scaling to a Reported $8.1BN Exit to Doordash, Building Teams not Families, The Difference Between Trust and Safety Within Companies, How To Use Compen Miki Kuusi is the CEO of Wolt and Head of DoorDash International. In 2014 Miki founded Wolt with a mission to turn the smartphone into a remote controller for life, starting with delivering your favorite restaurant food, to you at ...
11.25.2022 20VC: When to Make Your First Growth Hire? Senior or Junior? How To Onboard Them? How To Monitor Their Progress? from Growth Leaders @ Facebook, Instagram, Lyft, Instacart, Miro and more Casey Winters is the Chief Product Officer at Eventbrite. Prior to Eventbrite, Casey led the growth product team at Pinterest. Before Pinterest, Casey started the marketing team at Grubhub and scaled Grubhub’s demand-side acquisition and retention strategies. Elena Verna is ...
11.23.2022 20VC: Why Operating Experience Becomes Irrelevant Fast and Operators Often Give Bad Advice to Founders, Is Silicon Valley Really Dead? Are Gen Z the Most Entitled Employees? What Will Happen to a Gene Jeffrey Katzenberg is an entertainment industry executive and entrepreneur, who throughout his career has repeatedly reshaped the media landscape. Jeffrey co-founded DreamWorks SKG, serving as CEO of DreamWorks Animation, which he grew into the world’s largest animation studio, known for ...
11.21.2022 20VC: Semil Shah on The Biggest Mistakes VCs and LPs Made Over the Last 24 Months, Why LP Churn is Coming, Core Lessons on Scaling from $1M Haystack Fund I to Today and How To Find, Win and Manage LPs Semil Shah is the Founder of Haystack, one of the leading pre-seed and seed firms of the last decade. Among Semil's portfolio include the likes of DoorDash ($DASH), Instacart, Hashicorp ($HCP), Opendoor ($OPEN), Figma (acquired by Adobe), Carta and many ...
11.18.2022 20VC Rising Star: Why Founders Should Expect More From Their VCs \| How To Know Pre-Investment Whether a VC Will Be Valuable and How to Get the Most Value Out of Them \| Is There a Misalignment Between Oana Olteanu is a Partner @ SignalFire where she focuses on enterprise software at Seed, Series A and Series B. Prior to joining SignalFire, Oana was at Scale Venture Partners where she invested in applied ML and developer tooling. Oana ...
11.16.2022 20 Sales: The Ultimate Guide to Sales Onboarding for New Sales Reps and Sales Leaders, The Biggest Red Flags in the First 30 Days & What Can Be Done to Set Them Up for Success with Leaders from Figma, Oliver Jay (OJ) is one of the most successful sales leaders of the last decade. Most recently, OJ spent 6 years as CRO @ Asana and grew the team from 20 to over 450, becoming a master in sales onboarding ...
11.14.2022 20VC: ARK Invest's Cathie Wood on Why ARK Has Not Had More Outflows Despite Performance, How the Global Tech Equities Market Will Go From $7Trn to $210Trn in 8-10 Years, The Future for Facebook and Ho Cathie Wood is the CEO & CIO @ ARK Invest, focusing solely on disruptive innovation, primarily in the public equity markets. ARK has become renowned for opening up its research and becoming a ‘sharing economy’ company in the asset management ...
11.11.2022 20VC: Why Market Size is Everything \| Three Signs of a Bull Market and How To Remain Disciplined \| Why Investing is a Young Person's Game \| The Secret to Negotiation \| Missing a $200M Opportunity in N Martín Escobari is Co-President, Managing Director and Head of General Atlantic’s business in Latin America. Martín is Chairman of the firm’s Investment Committee and also serves on the Management and Portfolio Committees. Before joining General Atlantic in 2012, Martín was ...
11.09.2022 20 Product: Hugo Barra on Lessons Building Hardware Products at Android, Xiaomi, Oculus, and Detect; Feature Kings vs. Budget Kings; 996 Work Culture in China; There Are No MVPs in Hardware; The 3.5-H Hugo Barra is the OG of consumer hardware of the last decade. In Hugo's current position, he is the CEO @ Detect, building tools that empower people to understand their health and make informed, timely decisions. Before Detect, Hugo spent ...
11.07.2022 20VC: Coinbase's Brian Armstrong on Real vs Fake Emergencies, Coinbase's Failed NFT Launch, The Politicisation of Leadership, Why This Crypto Winter is Different From The Past & Brian's Development an Brian Armstrong is the Co-Founder and CEO @ Coinbase, the easiest place to buy and sell cryptocurrency. Over the last 10 years, Brian has led Coinbase to today, a public company with over 3,500 employees and revenues of over $7.5BN ...
11.04.2022 20VC: Michael Mauboussin on Good vs Bad Investment Decision-Making Processes, How To Improve Your Process, How To Know When it Needs Improving and The Single Biggest Mistakes People Make In Their Deci Michael Mauboussin is Head of Consilient Research at Counterpoint Global. Previously, he was Director of Research at BlueMountain Capital, Head of Global Financial Strategies at Credit Suisse, and Chief Investment Strategist at Legg Mason Capital Management. He is also the ...
11.02.2022 20VC: The GoPuff Memo: Why 10-15 Minute Delivery is an Unsustainable Model, The Plan to Make GoPuff Profitable by 2024, Mistakes Made in Europe and What the Europe Plan Should Have Been and What Does Raf Illishayev is the Co-Founder and CEO @ GoPuff, one of the market leaders delivering daily essentials in minutes. GoPuff’s latest funding round priced the company at a reported $8.9Bn in March 2021 and to date, Rafael has raised over ...
10.31.2022 20VC: Founders Fund's Brian Singerman on The Price Mismatch Between Public vs Private, Why Now Is Not The Best Time To Be Investing, Why Brian Never Thinks About Reserves and Believes in Cross-Fund In Brian Singerman is a Partner @ Founders Fund, one of the best-performing funds of the last two decades. Among their portfolio, they have the likes of Airbnb, Facebook, Stripe, Anduril, and many more generational-defining companies. As for Brian, he has ...
10.28.2022 20VC: Chris Sacca, Chamath Palihapitiya, Gary Vee, Brad Gerstner and more on Their Relationship To Money, How It Has Changed with Time and Wealth, How They Bring Up Their Children To Engender the Same Chris Sacca is the Founder and Chairman @ Lowercase Capital, one of the best performing funds in the history of venture capital with a portfolio including Uber, Stripe, Twitter, Instagram, Twilio, Docker and many more. From interviewing some of the ...
10.26.2022 20Growth: Biggest Growth Lessons from Reddit and Zynga on Scaling to Millions of Users \| Why, When and How To Hire Your First Growth Hires \| The Biggest Mistakes Founders Make In Hiring, Onboarding an Vaibhav Sahgal is VP of Consumer Product @ Reddit where he has been for close to 5 years. Prior to his leading consumer product, Vaibhav spent 3 years as Head of Growth at Reddit. Before Reddit, Vaibhav spent an incredible ...
10.24.2022 20VC: Uber's Journey to Becoming the Most Valuable Private Tech Company in History, Raising $3BN From Saudi in Just 60 Days, Uber's $30BN Mistake in Food Delivery, Why Recent Uber M&A Will be the Wors Emil Michael is the Former Chief Business Officer at Uber and is commonly referred to as Travis Kalanick's right-hand man. At Uber, Emil was instrumental in raising nearly $15BN from some of the largest investors in the world, making Uber ...
10.21.2022 20VC: Why 75% of Active Investors Will Disappear in the Next Few Years, The Death of "So So" Venture Firms is Coming, The Rise of Blackstone of Venture Firms and What That Does To Venture Returns, How Kyle Harrison is a General Partner @ Contrary and one of my favorite writers on the venture space with his blog, Investing 101 2.0. Before joining Contrary, Kyle worked in the ranks of some of the biggest and best names ...
10.19.2022 20 Sales: How To Structure The Interview Process for All Sales Reps, The Must-Ask Questions When Identifying Potential Sales Talent & The 3 Biggest Mistakes Founders Make When Hiring Their First Reps Lauren Schwartz is Vice President of Enterprise Sales at Fivetran, the leading platform for modern data movement. She has helped scale Fivetran's enterprise business from its infancy to a team of nearly 100, while more than tripling enterprise revenues. Previously, ...
10.17.2022 20VC: Dropbox's Drew Houston on Leadership; Hiring, Firing, Breakpoints in Company Scaling, The Story of Nearly Getting Acquired by Steve Jobs and Apple, How Founders Should Think Through Potential In Drew Houston is the Co-Founder and CEO @ Dropbox, for over 700 million users and +600,000 teams, Dropbox is the choice for storing and sharing their most important files. Prior to their IPO in 2018, Drew raised funding from some ...
10.14.2022 20VC: Why The CEO Should Make As Few Decisions As Possible, The Trade-Off Between Freedom and Raising Big From VCs & Why Our Jobs Are Not As Hard As We Think and How To Assess Talent and Potential As Tristan Handy is the Founder and CEO @ dbt, a data transformation tool that enables data analysts and engineers to transform, test and document data in the cloud data warehouse. To date, Tristan has raised over $400M from the likes ...
10.12.2022 20 Product: Spotify's Gustav Söderström on Why Product is 100% Science and 0% Art, Why You Should Look at the Competition and then Do Something Completely Different & Why Talk is Cheap and Product Tea Gustav Söderström is Spotify’s Chief Research & Development Officer. He has the CPO & CTO responsibility, overseeing the product, design, data, and engineering teams at Spotify and is responsible for Spotify’s product strategy. Gustav is also an entrepreneur and investor ...
10.10.2022 20VC: Altimeter's Brad Gerstner on Why Supercycles and the Powerlaw is the Most Important Thing In Investing, Why Portfolio Diversification is the Opposite of Risk Mitigation and The #1 Question Brad Brad Gerstner is the Founder and CEO of Altimeter, a life-cycle technology investment firm that manages public and private portfolios. Brad has personally participated in more than 100 IPOs as a sponsor, anchor, and investor. Brad’s notable deals include Snowflake, ...
10.07.2022 20VC: Kevin Weil on The Biggest Lessons from Leading Product at Instagram and Twitter \| How Working With Kevin Systrom Impacted His Approach To Product \| 3 Things Instagram Did To Make Stories So Succ Kevin Weil is President of Product and Business @ Planet and Operator in Residence @ Scribble Ventures. In the past, Kevin has been Head of Product at Twitter, Instagram, and Novi (the digital currency effort within Facebook). During his seven ...
10.05.2022 20VC: The Rippling Memo: Bedrock's Geoff Lewis on The Conviction Building Process to Write a $200M Check and Co-Lead Rippling's Series D \| Why No Competitor Can Out Execute Rippling \| Uncapped SAFE's Geoff Lewis is a Founder and Managing Partner of Bedrock, one of the breakout and new venture firms of the last decade, famously in search of narrative violations. He serves or has served on the Board of Directors for companies ...
10.03.2022 20VC: Rippling's Parker Conrad on The Four Main Benefits From Building a Compound Startup \| Why There Should Never Be a Trade-Off Between Speed and Quality \| How Zenefits Gave Parker a Chip on the Sho Parker Conrad is the Founder & CEO @ Rippling, the company that lets you easily manage your employees’ payroll, benefits, expenses, devices, apps & more—in one place. To date, Parker has raised over $697M for Rippling from some of the ...
09.30.2022 20VC: Lessons from Alfred Lin and Ron Conway \| Why the World Does Not Want Your Startup To Exist and How the Best Founders Fight It \| How To Build Moats and Defensibility Against Large Incumbents with Tarek Mansour is the Founder and CEO @ Kalshi, the first regulated exchange where you can trade directly on the outcome of events. Tarek has raised funding from some of the best including Alfred Lin @ Sequoia, Ali Partovi @ ...
09.28.2022 20Growth: Hubspot CMO Kipp Bodnar on Why the Best Marketers Think Like VCs \| Why the Best Companies Do Not Start with Product Marketing \| New Channels; When To Do, How Much To Spend, How To Test, When Kipp Bodnar is the Chief Marketing Officer of HubSpot, where he sets HubSpot’s global inbound marketing strategy. Prior to his role as CMO, Kipp served as VP of Marketing at HubSpot, overseeing all demand generation activity worldwide and building out ...

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