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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: Venture Capital | Startup Funding | The Pitch

Release Date: 10/08/2021

20VC: AppLovin’s Co-Founder & CEO, Adam Foroughi on How AppLovin Might Be The Venture Capital Industry’s Biggest Miss, How To Run a 1,000+ Organisation with Very Few Meetings & Balancing the Demands of Wall St with Long Term, Sustainable Growth show art 20VC: AppLovin’s Co-Founder & CEO, Adam Foroughi on How AppLovin Might Be The Venture Capital Industry’s Biggest Miss, How To Run a 1,000+ Organisation with Very Few Meetings & Balancing the Demands of Wall St with Long Term, Sustainable Growth

The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

is the Co-Founder and CEO @ , the company that allows developers to market, monetize, analyze and publish their apps. Under Adam's leadership, he has taken the company public, grown the team to over 1,000 people around the world, and scaled revenue in 2020 to $1.5Bn. Prior to AppLovin, Adam founded two companies—Lifestreet Media and Social Hour, and before that Adam started his career as a derivatives trader. In Today’s Episode with Adam Foroughi You Will Learn: 1.) How Adam made his way into the world of startups and came to found one of the world's largest gaming, advertising and...

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20VC: The Contentful Memo: Point Nine's Christoph Janz on The Cold Email That Led to a Unicorn Investment, How To Approach Market Sizing and Timing & The Pros and Cons of Pre-Emptive Rounds, When To Do Them vs When Not To? show art 20VC: The Contentful Memo: Point Nine's Christoph Janz on The Cold Email That Led to a Unicorn Investment, How To Approach Market Sizing and Timing & The Pros and Cons of Pre-Emptive Rounds, When To Do Them vs When Not To?

The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

is the Co-Founder and General Partner @ , one of Europe's leading early-stage firms with a portfolio including the likes of Zendesk, Algolia, Revolut, Nex Health, Loom and of course, Contentful. Prior to co-founding Point Nine, Christoph was a prolific angel investor and also the Co-Founder @ Pageflakes, leading the company from inception to their acquisition by LiveUniverse in 2008. Christoph is also one of the most thoughtful writers in SaaS and you can find his writing here. In Today’s Episode with Christoph Janz You Will Learn: 1.) How did a cold email from the solo founder of...

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20VC: Eugene Wei on 20VC: Eugene Wei on "Status as a Service", Why Networks Grow and Stop Growing, The Worst Design Choices Social Media Incumbents Have Made & The Next 10 Years of Media and the Metaverse

The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

is one of my favorite thinkers, writers, and strategists in tech today. Having spent the majority of his professional career at consumer internet companies, Eugene started his career with a 7-year stint at Amazon with a focus on product. He then joined Hulu leading the product, design, editorial, and marketing teams. Post Hulu, Eugene co-founded Erly, later acquired by Airtime, and then joined Flipboard as Head of Product. Finally, Eugene's last position was with Oculus as Head of Video. You have to check out Eugene's blog and can find his writing here. In Today’s Episode with Eugene Wei...

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20Growth: Top Growth Lessons from the Early Facebook, Twitter and Quora Days, The Most Important Question to Ask When Building Your Growth Team, How To Test For True Candidate Depth and Quality When Hiring for Growth with Andy Johns, Venture Partner @ Unu show art 20Growth: Top Growth Lessons from the Early Facebook, Twitter and Quora Days, The Most Important Question to Ask When Building Your Growth Team, How To Test For True Candidate Depth and Quality When Hiring for Growth with Andy Johns, Venture Partner @ Unu

The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

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20VC: Thrive Capital's Kareem Zaki on The One Rule That Drives Investment Decision-Making and Focus at Thrive, Why Every Large Institution Will Enter Venture Capital Over the Next Decade and How To Create a Firm Culture That Attracts The Best Young Talent show art 20VC: Thrive Capital's Kareem Zaki on The One Rule That Drives Investment Decision-Making and Focus at Thrive, Why Every Large Institution Will Enter Venture Capital Over the Next Decade and How To Create a Firm Culture That Attracts The Best Young Talent

The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

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20VC: The Anduril Memo: Founders Fund's Brian Singerman on What Makes Palmer Luckey One of the Greatest Innovators in History, Why It Is BS The DOD Do Not Want To Work With Silicon Valley & Why in Venture You Have To Play A Different Game to the Hedge Fun show art 20VC: The Anduril Memo: Founders Fund's Brian Singerman on What Makes Palmer Luckey One of the Greatest Innovators in History, Why It Is BS The DOD Do Not Want To Work With Silicon Valley & Why in Venture You Have To Play A Different Game to the Hedge Fun

The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

is a General Partner @ , one of the most prominent venture firms of the last decade with a portfolio including Anduril, SpaceX, Tesla, Palantir, Stripe, Affirm, Airbnb, Facebook, and many more. As for Brian, he has led investments in the likes of Affirm, Oscar Health, Wish, Asana, Oculus, and Postmates to name a few. Brian also sits on the board or is an observer to The Long Term Stock Exchange, Solugen, Cloud9, Modern Health, and of course, Anduril. Prior to Founders Fund, Brian spent a very successful 4 years as an engineer and executive at Google. In Today’s Episode with Brian...

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The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

and founded in 1983. Under their leadership, they have built Accel into one of the most prominent venture firms of the last 4 decades. Starting with Arthur, as the lead investor, Arthur has helped management teams develop companies into market-defining leaders over an incredible four decades. Prior to co-founding Accel, Arthur was a General Partner of Adler & Company with his career in venture starting at Citicorp Venture Capital.  As for Jim, Jim has been the lead director of more than 50 successful companies. He was instrumental as a founder/mentor of Accel London and in the...

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The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

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20VC: Mac the VC on the Journey from Homeless To Becoming A VC, What It Takes To Raise a Fund on Twitter, Why the Venture World is F***** Up and How Institutional LPs Need To Change show art 20VC: Mac the VC on the Journey from Homeless To Becoming A VC, What It Takes To Raise a Fund on Twitter, Why the Venture World is F***** Up and How Institutional LPs Need To Change

The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

 is the founder and managing partner of , a pre-seed fund that invests outside of large tech ecosystems, with a concentrated portfolio approach being the first check with up to $250K. Mac's journey into venture is nothing short of inspirational, Mac went from being homeless to being an engineer to founding his own companies to today, raising Rarebreed largely on Twitter. In Today’s Episode with Mac the VC You Will Learn: 1.) How Mac went from being homeless to becoming an engineer and starting his own company? How did his time operating lead to his becoming a VC and building his...

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The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

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Anthony 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