20VC: Squarespace Founder, Anthony Casalena on Scaling Squarespace from Dorm Room To Public Company with over $700M in ARR, The Decision to Direct List over Traditional IPO or SPAC & What Changes When You Go Public?
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Release Date: 10/08/2021
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
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
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
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
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, "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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20VC: Founders Fund's Trae Stephens on Why The Most Competitive Deals are the Worst, Why No Company is Successful Because of their VC, Why We are Making ZIRP Mistakes Again Today, Why Loss Ratio is BS and Upside Maximisation is Everything
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Trae Stephens is a Partner at , one of the world's leading funds where he has worked with some of the best and backed the likes of Palmer Luckey with Oculus and @ Flexport since the very early days. Trae is also Co-founder and Executive Chairman of Anduril Industries, a defense technology company focused on autonomous systems, and Co-founder of Sol, a next-generation wearable e-reader. Previously, Trae was an early employee at Palantir Technologies, where he was also an integral part of the product team, leading the design and strategy for new product offerings. In Today's Episode with...
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20VC: The Memo: The $23BN Company You Might Not Have Heard Of: Tradeweb, The Story of 27 Years of Compounding Growth Leading to the Market Leader with $1.4BN in Revenue and 50% EBITDA Margins
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Billy Hult is Chief Executive Officer of (Nasdaq: TW), as Billy puts it, they are the "electronic interface that connects Citadel and Goldman". They are also one of the most under the radar but incredible businesses of the last 20 years. Through no glitz acquisitions or specific moments, TradeWeb has compounded organic growth for the last 27 years to today, with a market cap of $22BN. In Today's Episode with Billy Hult: 1. From Betting Shop Worker to Public Company CEO: How would Billy's teachers and parents have described the young Billy? Why does Billy think it is so important to...
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20VC: a16z's Chris Dixon on Who Will Win the Next Generation of Venture, The Two Ways to Make Great Venture Investments and Find the Best Entrepreneurs & Why AI Will Strengthen the Position of the Incumbents Moving Forward
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Chris Dixon is a General Partner at Andreessen Horowitz, one of the leading venture firms of the last decade with investments in Oculus (acquired by Facebook), Coinbase, and many more. Chris also founded and leads a16z crypto, a division of the firm that he has grown from $300 million in 2018 to more than $7 billion of committed capital. Due to his many successes, Chris was named #1 on the Forbes Midas List in 2022. In Today’s Episode with Chris Dixon We Discuss: From Founder to Leading GP in Venture: How did Chris make his way into the world of venture and startups? When did he...
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20VC: Lessons from 32 Years of Fund Investing | Why Exits Will Be Larger & Funds Sizes Bigger | Top Reasons to Turn Down Potential Fund Investments | Fees, Carry, Deployment Pace; What Do LPs Inspect When Fund Investing with David Clark, CIO @ Vencap
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
David Clark is the CIO of , one of the leading fund of funds in the venture landscape. David has been at Vencap for 32 years and has been an LP his entire career. In Today's Episode with David Clark We Discuss: 1. From Unemployed Student in Love to Leading LP: How did a girlfriend lead to David taking his first steps into the world of fund investing? What does David know now about fund investing that he wishes he had known when he started? 2. Is Being an LP Harder than Ever Before: Does David agree with , "venture has transitioned from a boutique high margin business to a low...
info_outlineAnthony Casalena is the Founder & CEO @ Squarespace, the company that allows you to create a website, sell anything and market your business. To date, Anthony has raised over $948M for the company from the likes of General Atlantic, Index Ventures, Tiger Global; culminating in their IPO in May 2021. Despite the incredible size and scale of Squarespace today, Anthony started the company from his dorm room in 2003 and bootstrapped the business for many years to today with over 1,100 employees around the world.
In Today’s Episode with Anthony Casalena You Will Learn:
1.) How Anthony came to start Squarespace from a dorm room and turn it into a public company with over 1,200 employees globally?
2.) Why did Anthony decide to bootstrap with Squarespace for over 6 years when the company was scaling fast and profitable? How was Anthony's mindset impacted by the efficiency of bootstrap scaling? How did Anthony's mindset change when Squarespace raised their first large round? How does Anthony advise founders today on raising venture vs bootstrapping?
3.) Why did Anthony decide to do the direct listing over the more traditional IPO or a SPAC? How does Anthony advise other founders contemplating the same exit choices? How does Anthony personally describe this chapter of the company? Does he enjoy being a public company CEO? What are the best elements? What are the worst?
4.) E-Commerce has been a massive driver for growth for Squarespace, how does Anthony feel about the future of e-commerce on Squarespace? Only 1% of Squarespace's $700M ARR comes from enterprise, does enterprise hold a meaningful position in the future of the company? What are the core challenges of moving into enterprise? How does the company need to change?
5.) With the growth of the company, how has Anthony changed his style of leadership? What are his biggest strengths? What are his biggest weaknesses? What are the most obvious breakpoints in the scaling of companies?
Item’s Mentioned In Today’s Episode with Anthony Casalena
Anthony’s Favourite Book: Thinking Fast and Slow