 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 

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

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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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 Discuss:   From Online Forum to the Founding of a $5BN Company:     How did a horrible customer service experience prompt Girish to start Freshworks? What was the aha moment?   What were Girish’s biggest challenges founding Freshwork in 2010?   How was building the first product? What worked? What didn’t work?     Biggest Lessons on Product, Pricing and People Scaling to $5.2BN:     Why does Girish believe Indian companies have to win globally before winning India?   What were Girish’s biggest mistakes scaling Freshworks? What were his lessons?   Why does Girish believe starting high and going down never works in software?   When does Girish think is the best time to build the second product?   How did Freshworks lose against Slack? What did he learn from the experience?     The Biggest Lessons to Becoming the Best Leader:     How has Girish’s leadership style changed over time?   What were Girish’s biggest hiring mistakes?   What was Girish’s biggest challenge in building culture during COVID?   What is one piece of advice Girish believes every CEO should follow?     How India Will Become a Global Player in Tech, AI and Football:     Why does Girish believe now is the time for India tech?   What are the most common misconceptions of India tech?   What traits does Girish look for in founders he invests in?   What was Girish’s biggest investment mistake? What did he learn from it?  

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 Mathru

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 her takeaways?   What was Vickie’s business model at Polyvore that eventually led to the $200M acquisition by Yahoo?     Lessons from Scaling 100+ Companies in Sequoia     What does Vickie believe are the biggest mistakes early stage founders make when telling stories?   Which 2 components does Vickie believe every great product mission should include?   How should pre-product-market fit founders set their north star metric?     Perfecting Product Strategy     What was Vickie’s biggest product mistake? What were her lessons?   Why does Vickie think the best product people build less product?   What is Vickie’s advice to product leaders starting their first day on the job?   What are the most common mistakes founders make when hiring product teams?     Product-Market Fit Masterclass     Why does Vickie believe product-market fit is a journey not a destination?   What are the biggest reasons founders fail to get product-market fit?   What are the 3 types of product-market fit?   How does Vickie advise founders to differentiate themselves in competitive markets?   What is Vickie’s framework for competing against incumbents?    

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 @ S

 Sam Altman 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.   Brad Lightcap 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 met Sam and before that led finance and operations initiatives at Dropbox.    In Today's Episode with Sam Altman and Brad Lightcap We Discuss:   1. The Partnership: The Most Powerful Double Act in Tech:    How did 25 people rejecting OpenAI's CFO positions 6 years ago, lead to Brad joining OpenAI before Sam even did? What did he see that the world did not?  What does Brad think is Sam's biggest superpower that the world does not know? What does Sam think it Brad's biggest superpower that the world does not now?  How do decisions get made between Brad and Sam? How do they decide what to delegate vs what not to? What is the most recent disagreement they had? How did they resolve it?    2. The Next 12 Months for OpenAI: Bottlenecks, Compute and Commoditisation:    What are the core bottlenecks facing OpenAI in the next 12 months?  How does Sam believe we solve the fundamental problem of compute?  What is the single biggest barrier to the quality of models improving?  What is the end state for the model landscape? Will models become commoditised?    3. OpenAI: The Fastest Scaling Company in History:    What has been the secret to how OpenAI has scaled to $2BN in revenue in 24 months?  Why does Sam believe that he is "not a great operator"? What drives this thinking?  What have been the first things to break in the scaling of OpenAI?  What do Brad and Sam know now about the scaling that they wish they had known at the start?  Why does OpenAI lean towards hiring more experienced people in the team?    4. How to Invest and Operate in a World of OpenAI:    What single question can founders ask that will reveal if they will be steamrolled by OpenAI?  Does Sam believe huge numbers of companies will be steamrolled by OpenAI?  For investors, is there money to be made investing in the application layer of AI today?  What question should all businesses be asking about how to adopt and use AI in their business?    5. Sam Altman: AMA:    What have been the single biggest lessons Sam has learned from the founders he has invested in?  Which founders has he learned the most from? What did he learn from each?  What is Sam most concerned about in the world today? Why what?  What unexpected traits or characteristics does Sam most look for in the founders he invests in?  Why does Sam say that he is not happy but he is grateful?          

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 Compan

 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? What was the best?  What are Sam's biggest tips to people picking the rocketship they will join?    2. Who, What and When to Hire:    When is the right time to hire your first sales rep?  Should the founder be the one to create the sales playbook?  What is the right profile for the first sales hire?  Does it matter if the new hire has domain experience?  Why does Sam always advocate to hire through network and not recruiters?    3. How to Hire the Best Sales Reps:    What are the questions Sam always asks in interviews with sales hires?  Does Sam do case studies with candidates? What is he looking for?  What are the biggest green and red flags a candidate can show in an interview process?  What are the biggest mistakes founders make when hiring sales teams?    4. How to Have the Best Performing Sales Team:    What are the three ways to measure the success of a rep in the first 30-60 days?  Why does Sam believe most startups are doing outbound wrong? What should they change?  Why does Sam believe demand gen is the bottleneck for all companies?  What can be done to solve the demand gen challenge?  How does outbound change in a world of AI?  

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 B

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 Entrepreneurship     How did Kevin’s early life shape his career? How would his parents and teachers describe him?   Does Kevin agree that successful entrepreneurs always show signs early?   What does Kevin think about luck vs. skill? Why does Kevin think that most things are out of your control as an entrepreneur?     Lessons from Founding 10+ Companies Worth $27BN     Does Kevin agree the best CEOs are also the best fundraisers?   What were Kevin’s biggest lessons from scaling DoubleClick from 20 to 2000 employees?   What was Kevin’s a-ha moment behind Business Insider? What was the reason behind its success?   Why does Kevin believe the best founders are always in unfamiliar fields?     Incubating World’s Best Companies     How does Kevin allocate resources between incubations vs. investments?   What are the biggest commonalities between successful companies at AlleyCorp?   Is Kevin a market-led or people-led investor?   What does Kevin think is the most important element in achieving product-market fit?   What was Kevin’s biggest miss on selecting founders? What were his takeaways?     Current State of Venture     Why does Kevin believe venture is more competitive now than ever before?   What does Kevin know now that wish he’d known when he started investing?   Does Kevin agree rich investors make better investors?   Why does Kevin not care about ownership?   Does Kevin agree with Doug Leone that venture has transitioned from a high boutique margin industry to a low margin commoditised industry?   Does Kevin agree with Peter Fenton that price is a mental trap?    

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 

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

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