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20VC: Firstmark's Rick Heitzmann on The Rise of Pre-Emptive Rounds, His Biggest Learnings From The Pinterest Board, 2 Things VCs Can Do To Prepare Their Companies For The Downturn and Why Now Is A Good Time to Be Contrarian and Invest In Consumer

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

Release Date: 11/11/2019

20Growth: Inside Dropbox, Salesforce & Heroku's Product-Led Growth Engine; What Works & What Doesn't | Why Startups Doing Paid Under $100M ARR are not PLG | Why PLG is a Business Model, Not a Go-To-Market Motion with Adam Gross, Former CEO @ Vimeo show art 20Growth: Inside Dropbox, Salesforce & Heroku's Product-Led Growth Engine; What Works & What Doesn't | Why Startups Doing Paid Under $100M ARR are not PLG | Why PLG is a Business Model, Not a Go-To-Market Motion with Adam Gross, Former CEO @ Vimeo

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

Adam Gross is one of the masters of product-led growth (PLG). Most recently, Adam was Vimeo's interim CEO. Before Vimeo, Adam was CEO of Heroku, which he joined after selling his startup, Cloudconnect in 2013. Additionally, Adam has held executive leadership roles at Salesforce and Dropbox, and has been an active angel investor & advisor to companies, including Buildkite, Cribl, and Tailscale. In Today’s Episode with Adam Gross We Discuss: PLG Tactics from Dropbox, Heroku and Salesforce: What were Adam’s biggest takeaways from his time at Salesforce? How did it shape his growth...

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20VC: Is Speed the Most Important Thing from 0-1 | Why Hiring Inexperienced People is Better | The Biggest Lessons Scaling Zip to $1.5BN Valuation with Rujul Zaparde, Co-Founder and CEO @ Zip show art 20VC: Is Speed the Most Important Thing from 0-1 | Why Hiring Inexperienced People is Better | The Biggest Lessons Scaling Zip to $1.5BN Valuation with Rujul Zaparde, Co-Founder and CEO @ Zip

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

Rujul Zaparde is the Co-Founder and CEO of Zip, the world’s leading Intake-to-Pay solution, adopted by leading enterprises and startups including Snowflake, Canva, Airtable, Webflow, and others. In 2023, Zip raised $100 million in a Series C round, valuing the company at $1.5 billion. Before founding Zip, Rujul was a Visiting Partner at Y Combinator and a product manager at Airbnb. In Today’s Episode with Rujul Zaparde We Discuss: From Airbnb PM to $1.5BN Founder How did Rujul’s first company fail? What were his lessons? What did Rujul learn from his time at Airbnb? How did...

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20VC: UiPath: The 10 Year Bootstrapping Journey that Turned into a $10BN Public Company | From a Dollar a Day to Romania's Richest Man | Happiness, Wealth, Risk and more with Daniel Dines, Co-Founder @ UiPath show art 20VC: UiPath: The 10 Year Bootstrapping Journey that Turned into a $10BN Public Company | From a Dollar a Day to Romania's Richest Man | Happiness, Wealth, Risk and more with Daniel Dines, Co-Founder @ UiPath

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

Daniel Dines is the Co-Founder @ , one of the most incredible journeys in startups. For 10 years, UiPath was a bootstrapped company that scaled to just $500K in revenue. Then it all changed, product market fit became obvious and the rest is history. The company went on to raise funding from , Accel, Kleiner Perkins and more. Today, the company is worth over $10BN, listed on the NASDAQ and does $1BN+ in revenue. In Today's Episode with Daniel Dines We Discuss: 1. From a Dollar a Day to Romania's Richest Man: How would Daniel's parents and teachers have described the young Daniel? How...

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20VC: Three Core Lessons Scaling Freshworks to a $5.2BN Market Cap | Biggest Product and Pricing Lessons from Scaling to $597M in ARR | How India Can Compete Globally in Tech and AI with Girish Mathrubootham, Co-Founder @ Freshworks show art 20VC: Three Core Lessons Scaling Freshworks to a $5.2BN Market Cap | Biggest Product and Pricing Lessons from Scaling to $597M in ARR | How India Can Compete Globally in Tech and AI with Girish Mathrubootham, Co-Founder @ Freshworks

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

Girish Mathrubootham is the founder and CEO of Freshworks, India’s first SaaS company to list on NASDAQ. Today, Freshworks has over $596M in ARR with a $5.27BN market cap, with investors like Accel Partners, Sequoia Capital, Tiger Global Management, and CapitalG. Girish is also a founding member of SaaSBOOMi, Asia’s largest community of founders and product builders, and has invested in over 60 startups. On top of that, Girish is also the Founder of Together Fund, a $150M fund focusing on Indian B2B companies going global from day 1. In Today’s Episode with Girish Mathrubootham We...

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20Product: Sequoia's Product-Market Fit Framework | Why the Best Product People Actually Build Less Product | Metrics 101, Good vs Great Product Strategy and more with Vickie Peng, Product Partner @ Sequoia Capital show art 20Product: Sequoia's Product-Market Fit Framework | Why the Best Product People Actually Build Less Product | Metrics 101, Good vs Great Product Strategy and more with Vickie Peng, Product Partner @ Sequoia Capital

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

Vickie Peng is a Product Partner at Sequoia and the co-creator of Arc, their company-building immersion programme for pre-seed and seed stage founders. Prior to Sequoia, Vickie was a product manager at Polyvore (acquired by Yahoo for $200M) and Instagram, where she grew SMB advertising from $200M to $1BN. In Today’s Episode with Vickie Peng We Discuss: Lessons from 15 Years in Product How did Vickie make her way into the world of product? How did Vickie turn a small side business into a massive revenue machine at TrialPay? How did Vickie scale Instagram SMB ads to $1BN? What were...

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20VC: OpenAI's Sam Altman and Brad Lightcap on The Future of Foundation Models: Will They Be Commoditised | How to Solve the Problem of Compute | Open vs Closed: Which Dominates and Why | Which Companies and Verticals Will Be Steamrolled by OpenAI show art 20VC: OpenAI's Sam Altman and Brad Lightcap on The Future of Foundation Models: Will They Be Commoditised | How to Solve the Problem of Compute | Open vs Closed: Which Dominates and Why | Which Companies and Verticals Will Be Steamrolled by OpenAI

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

is the CEO @ OpenAI, the company on a mission is to ensure that artificial general intelligence benefits all of humanity. OpenAI is one of the fastest-scaling companies in history with a valuation of $90BN and $2BN+ in revenue. Prior to OpenAI, Sam was the President and CEO @ Y Combinator and made angel investments in the likes of Airbnb, Stripe, Reddit, Pinterest, Asana and more. is the COO @ OpenAI and the man responsible for the incredible scaling of sales, GTM, partnerships and business to today being over $2BN in revenue. Before OpenAI, Brad was an investor at Y Combinator, where he...

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20Sales: The Biggest Sales Lessons Scaling Brex to $400M ARR, Why Startups are Doing Outbound Wrong and How to Fix It & Why Demand Gen is the Bottleneck for all Startups and How to Solve it with Sam Blond, Former CRO @ Brex show art 20Sales: The Biggest Sales Lessons Scaling Brex to $400M ARR, Why Startups are Doing Outbound Wrong and How to Fix It & Why Demand Gen is the Bottleneck for all Startups and How to Solve it with Sam Blond, Former CRO @ Brex

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

Sam Blond is the former CRO at Brex, where he led the company from near $0-$400M in ARR and a $12.5B valuation. Before Brex, Sam was VP of Sales at Zenefits, where he led the company from $0-$70M ARR in 2 years and a $4.5B valuation. Sam joined Founders Fund as a Partner in 2022 and recently left to focus more on operating. In Today's Episode with Sam Blond We Discuss: 1. Lessons From Scaling Brex to $400M ARR & Zenefits to $70M ARR: What are the secrets that very few people know, that led to the success of Brex and Zenefits? What was the single worst sales investment Brex made?...

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20VC: Are the Best CEOs the Best Fundraisers, Are the Best Founders Insiders or Outsiders to a Problem, Why Ownership Should Not Be a Focus in VC & The Biggest Lessons Scaling MongoDB to $26BN Market Cap with Kevin Ryan, Founder @ AlleyCorp show art 20VC: Are the Best CEOs the Best Fundraisers, Are the Best Founders Insiders or Outsiders to a Problem, Why Ownership Should Not Be a Focus in VC & The Biggest Lessons Scaling MongoDB to $26BN Market Cap with Kevin Ryan, Founder @ AlleyCorp

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

Kevin Ryan is one of the leading serial entrepreneurs and investors in New York. Previously he co-founded MongoDB, Business Insider, Gilt Groupe, Zola, Nomad Health, Pearl Health, and was the CEO of DoubleClick (Acquired by Google for $3.1B). Today, Kevin is the founder and CEO of AlleyCorp, a venture capital firm that incubates and invests in transformative companies in healthcare, diversified tech, robotics, and impact. Just yesterday, Alleycorp announced their $250M fund, their first ever external capital.  In Today’s Episode with Kevin Ryan We Discuss: Early Signs of...

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20VC: Postmates Founder Basti Lehmann on How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN, Why Great VCs Add No Value and VC Value Add is BS Marketing & Why The Biggest Companies in History Will be Born Today and Replace Incumbents show art 20VC: Postmates Founder Basti Lehmann on How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN, Why Great VCs Add No Value and VC Value Add is BS Marketing & Why The Biggest Companies in History Will be Born Today and Replace Incumbents

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

Basti Lehmann is the co-founder and former CEO of Postmates, the on-demand delivery service that raised over $900M from the likes of Tiger Global, Founders Fund, Spark Capital and Andreesen Horowitz. Following Uber’s $2.65BN acquisition in 2020, Basti founded TipTop, a platform for fast tech sales which Marc Andreesen led the $20M seed round for. In Today’s Episode with Basti Lehmann We Discuss: From US Immigrant to Billion Dollar Founder How did Basti start his career hacking AT&T? How did early hardships shape Basti’s work ethic? What were Basti’s biggest challenges...

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20VC: Oscar Health: How to Deal with a 94% Decline in Market Cap, 20VC: Oscar Health: How to Deal with a 94% Decline in Market Cap, "Why I Stood Aside as CEO" and The Rebound Journey to $5.8BN in Revenue with Mario Schlosser, Co-Founder @ Oscar Health

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

Mario Schlosser is the Co-Founder and Chief Technology Officer at . The public company that went public with a market cap of $7.1BN. Following a tumultuous time in the markets, their stock price dropped 94%. Today, the company has rebounded and has a market cap of $3.2BN with an astonishing $5.8BN of revenues. Before co-founding Oscar, Mario also co-founded the largest social gaming company in Latin America. In Today's Episode with Mario Schlosser We Discuss: 1. From German Middle-Class to Public Company Founder: How did Mario make his way into the world of tech and come to co-found...

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Rick Heitzmann is a Founder and Partner @ Firstmark Capital, one of the leading East Coast venture funds of the last decade with a portfolio including the likes of Airbnb, Pinterest, InVision, Shopify and Discord to name a few. As for Rick, he led the seed round for Pinterest and also led the deals from Firstmark in Ro, Riot Games, Draft Kings, Discord and Airbnb. Prior to founding FirstMark, Rick was an entrepreneur as a founding member at First Advantage which he helped grow and sell to First American (NYSE: FAF). Rick has been recognized by CB Insights and the New York Times as a Top 100 Venture Capitalist globally.

In Today’s Episode You Will Learn:

1.) How Rick made his way into the world of venture and came to found one of NYC's leading venture funds in the form of Firstmark?

2.) How did seeing the booms and bust of the macro impact Rick's investment mentality today? With the impending crash, what 2 things does Rick advise managers need to prepare their portfolio by doing? Does Rick agree with Bill Gurley in saying, "the biggest challenge of today is the over-supply of capital"?

3.) How has Rick seen his style of investing change over the last 20 years? How does Rick think about price sensitivity today? How has that changed over the years? How has Rick seen himself change and evolve as a board member? What does Rick believe makes the best board members? What advice would Rick give to someone who has gained their first board seat?

4.) How does Rick think about the structure of the Firstmark portfolio today? How important does Rick believe it is to have temporal diversification within the portfolio? How does Rick think about optimising investment decision-making processes at Firstmark? Why does Rick believe, despite the negatives, that attribution is fundamentally important?

5.) Does Rick believe that we are in a consumer bubble today? What are the core elements that pique Rick's interest when analysing a consumer investment today? How does Rick think about CAC's scaling way faster and higher than anyone expected? Why does Rick believe the duopoly of FB and Google is now over? Why does Rick believe that true venture size exits can still occur in consumer?

Items Mentioned In Today’s Show:

Rick’s Fave Book: Moneyball: The Art of Winning an Unfair Game

Rick’s Most Recent Investment: Crisp

As always you can follow HarryThe Twenty Minute VC and Rick on Twitter here!