20VC: The Chess.com Memo: The Most Untold Story in Startups; Scaling to $100M Revenue, 150M Members and 700 People, All with Zero Venture Funding | Erik Allebest, CEO @ Chess.com

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 mindset? What did Adam learn about customer acquisition at Dropbox? What would Adam most like to change about growth today? Product-Led Growth: The Fundamentals: What is growth? What is it not? What do founders get wrong about growth? Why does Adam think PLG is not for everybody? What do most great PLG businesses have in common? How are value propositions segmented in PLG? How can startups transition from individual to enterprise clients? Why does Adam think startups doing paid acquisition sub $100M aren’t actually PLG? The Secrets to Optimizing Growth Channels: What are the most common reasons fast-growing companies plateau? How does Adam advise founders on diversifying channels? What are the biggest mistakes founders make when scaling into enterprise? How should startups do effective product marketing in horizontal products? What is emotive & strategic marketing? How should startups balance both? How Angel Investing Changes How You View Companies: What are Adam’s top 3 pieces of advice for founders? What does Adam mean when he says you are either hiring a poet or a librarian? What are the biggest mistakes founders make when hiring? What was Adam’s biggest investment miss? What did he learn from it?

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 Rujul come to co-found Zip? What was the aha moment? What did Rujul wish he’d known when he started Zip? Standing Out in a Hyper-Competitive Market Why did Rujul pick such a competitive market? How did they stand out? Does Rujul think founders should focus on pain points or platform solutions on day one? What is Rujul’s advice to founders who are in the discovery process? Does Rujul agree with Trae Stephens @ Founders Fund that serial entrepreneurs doing B2B enterprise SaaS are wasting their talent? The Biggest Lessons Scaling Zip to $1.5BN Valuation Which key moment caused Zip to accelerate? Why does Rujul think speed is the most important element in startups? Why does Rujul not believe in design partners? Why does Rujul believe repeatability is the most important thing when pitching? Does Rujul think AI will destroy outbound sales? How to Hire & Manage Teams What was Rujul’s “rude awakening” building a sales team? What was Rujul’s biggest hiring mistake? What did he learn from it? How does Rujul decide where to focus his attention and resources? Why does Rujul believe younger managers are more creative?  

Daniel Dines is the Co-Founder @ UiPath, 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 Sequoia, 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 did Daniel first learn to code? Why was his first programming job on $300 per month the best? How did Daniel learn English by playing bridge with his friends? What was the a-ha moment for Daniel with UiPath? 2. Becoming a Billionaire: The Mental Journey: What does Daniel mean when he says everyone is a prisoner of their own mind? How does Daniel reflect on his own relationship to money? How did having absolutely nothing impact Daniel's relationship to risk? Why does Daniel think that he does not really experience or feel happiness? 3. 10 Years to $500K ARR: The Miracle Bootstrapping Journey: After 10 years, UiPath had just $500K in ARR, what was the one single moment that changed everything in 2014? How did raising the seed round change everything for Daniel? How did it change his approach to operating? What was the impact of having Sequoia invest? Does it change the game? Why did Daniel say no to them the first time they tried for the Series B? 4. Journey to a $10BN Public Company: The Crucible Moments: How did the company almost go bust when it spent $400M against a plan of $150M in 2021? What is the single proudest moment Daniel has of the 19 year journey with UiPath? What have been Daniel's biggest management lessons in scaling UiPath to $1BN in ARR? Knowing all that Daniel does today, what would he have done differently about the UiPath journey?

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?

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?  

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?    

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?

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?  

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 building Postmates? Lessons from Raising $900M How did Basti raise $20M from Marc Andreesen? How does Basti select which VCs to work with? Why does Basti think 99% of VCs are sheep? Why does Basti think great VCs add no value? Why does Basti think having to educate investors is a massive red flag? Selling Postmates for $2.65BN Why did Basti sell Postmates to Uber? How did the acquisition happen? Was there anything Basti would have done differently? What does Basti think makes Dara Khosrowshahi a great CEO? What is Basti’s biggest advice to founders on acquisitions? Future of AI: Startups or Incumbents? What does Basti think is the biggest challenge of LLMs today? Why does Basti think inference computing will be the future of AI? Why does Basti think incumbents can be replaced? Why does Basti think the biggest companies are being born today?  

Mario Schlosser is the Co-Founder and Chief Technology Officer at Oscar Health. 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 Oscar with Josh Kushner? Does Mario agree with Jensen Huang that "we should all have lower expectations"? What does Mario know now that he wishes he had known when he started Oscar? 2. Why Did Oscar Tank 94% in the Public Markets: What was the core reason why Oscar tanked 94% in the markets? What would Mario have done differently knowing all he knows now about public markets? Does Mario regret going public? What are the biggest pros and cons? 3. The Mental Challenge of a 94% Market Cap Decline: How did Mario mentally deal with the company being down 94%? What does he say to himself in the truly hard times? How did Mario use his co-founder, a coach and his family, to get through the really bad times? What are Mario's experiences like with anti-depressants? What worked? What did not? 4. Firing Yourself as CEO: Why did Mario decide to step aside as CEO? What was the decision-making process? On reflection, does Mario think he was a good CEO? Where was he good? Where was he bad? What are the biggest management pieces of advice that Mario thinks are BS?