20VC: Affirm Max Levchin on Why Grading Talent by Letter (A or B) is Total BS | How to Create a Culture of Post Mortems and Writing | Why You Should Only Study Failure Not Success & The Biggest Surprises Scaling to $18.7BN Market Cap

Jean-Denis Greze is Chief Technology Officer at Plaid where oversees global product business units across North America and Europe. Prior to joining Plaid, Jean-Denis was Director of Engineering at Dropbox. Jean-Denis is also a prolific angel investor with a portfolio including the likes of Nex Health, Merge.dev and Rupa Health to name a few. In Today's Episode with Jean-Denis Greze We Discuss: 1. The Journey to One of the Most Powerful CTOs: How JD made his way into the world of tech with his first role at Dropbox? How does JD analyse a Linkedin CV today? What are the signals of outperformers? What does JD know now that he wishes he had known when he started in tech? 2. Hiring the Best: 101: What are JD's single biggest lessons on hiring the best talent? What have been some of JD's biggest hiring mistakes? Why does JD believe founders need to be as good at firing as they are hiring? Does JD believe people can scale with the scaling of a company? If they do not scale, do you layer them or do you let them go? How does JD determine whether to bring in an external candidate vs promote someone from within? 3. Product Differentiation is not Sustainable: Why does JD believe that product differentiation is not sustainable? Why is UX as a moat BS? How does this lead JD to suggest Salesforce is a short in the public markets? Why does JD believe that Snowflake is also a short? What does Snowflake teach us about the different stages of product market fit? What are the biggest mistakes founders make when analyzing product market fit? 4. Remote Work, Titles and Entitlement: Why does JD believe most tech employees treat their employer in the same way French citizens treat the French government? How does JD analyse the impact of remote work on both productivity and culture? Why does JD believe titles are BS in the beginning but matter with scale? Why does JD believe that you should not hire for the long term?

21 Jul 202350min

Lauryn Isford is the Head of Product Growth at Notion, managing Notion's product-led growth engine and self-serve business. Before Notion, she led growth at Airtable, and previously worked on growth teams including Meta, Dropbox, and Blue Bottle Coffee. Lauryn is an active angel investor and advisor supporting companies building product-led go-to-market motions.  In Today's Episode with Lauryn Isford: 1. From Blue Bottle to Airtable and Notion: How did Lauryn first make her way into the world of product and growth? What are 1-2 of her biggest takeaways from Dropbox, Facebook and Blue Bottle? What does Lauryn know now that she wishes she had known when she started? 2. What is Growth: 101: How does Lauryn define growth? What is it not? When is the right time to make your first growth hire? What profile should your first hire in growth be? What are the single biggest mistakes founders make when hiring growth teams? 3. Mastering the Onboarding Experience: What are the core elements of a successful onboarding experience? How important is time to value in onboarding today? What are the biggest mistakes product teams make in company onboarding? What is the most effective onboarding technique and workflow in PLG today? Why are 90% of current onboarding's done badly? 4. Making Growth work with the Rest of the Org: What are the single biggest barriers to growth and product working together well? What can leaders do to make their growth teams work well with product teams? How can growth teams experiment and test with product without messing up codebases?

19 Jul 202347min

Dave Clark is the CEO of Flexport, the global freight forwarder and logistics platform that has now raised over $2.5BN to build the category leader. Prior to Flexport, Dave began his career at Amazon in 1999 as an Operations Manager, working his way up to become the CEO of Amazon’s worldwide consumer business in 2021. By the time Dave left, he was responsible for over 1 million employees. Dave spearheaded the launch of Amazon Robotics and grew the company’s logistics divisions to include Amazon’s own planes, trailers, and last-mile delivery vehicles through Amazon’s own delivery network (which today ships more packages than FedEx and UPS). Huge thanks to Ryan Peterson for some amazing question suggestions today. In Today's Episode with Dave Clark We Discuss: 1. From Operations Manager to CEO @ Amazon: How did Dave Clark make his way into the world of startups with Amazon in 1999? What are 1-2 of his biggest lessons from spending 23 years at Amazon? What are 1-2 of his biggest takeaways from working alongside Jeff Bezos for 23 years? 2. How Big Leaders Make Big Decisions: What is Dave's decision-making framework when it comes to big decisions? What is the biggest decision Dave made that went wrong? How did it impact his mindset? How does Dave think through prioritisation as a leader today? What are the biggest mistakes founders make when it comes to focus? 3. How Big Leaders Hire Big Talent: What are 1-2 of Dave's biggest lessons on what it takes to acquire the best talent? Does Dave believe that people can scale with the scaling of the company? How does Dave think through the challenge of promoting internally vs bringing in external talent? Why does Dave like to hire people straight out of college? What are the benefits? 4. How Big People Deal with Big Problems: Kids, Money and Ego What are 1-2 of Dave's biggest lessons when it comes to parenting? How does Dave think about giving his kids the same hunger and ambition, when they are brought up in such affluent environments? How does Dave assess his own relationship to money? How has it changed over time? What does a truly great marriage mean to Dave? Where do so many go wrong in trying to find work-life balance?

17 Jul 202343min

Sheel Mohnot is a Co-Founder and General Partner @ Better Tomorrow Ventures, a $225M fund that leads rounds in pre-seed and seed-stage fintech companies globally. Sheel and Jake (his co-founder) invested for many years together before founding BTV and wrote checks into Mercury, Flexport, Ramp, and Hippo Insurance to name a few. As for Sheel, before BTV he ran 500 Fintech for close to 7 years, and before that was a founder, founding two companies, both of which were acquired. In Today's Episode with Sheel Mohnot We Discuss: 1. VC Needs to Change: Why does Sheel believe that VCs should have smaller funds? What are the biggest misalignments between founders and VCs today? What are the biggest points of friction between VCs and their LPs today? 2. VC in 10 Years Time: Who are going to be the winners in venture in 10 years time? Who are going to be the losers? Will micro-funds be bigger or smaller as a segment of the ecosystem? Will solo-GPs be bigger or smaller? Were they a zero-interest rate phenomenon? 3. The Errors of a Bull Market: What does Sheel believe are the single biggest mistakes made by VCs between 2020-2022? Did Sheel take liquidity off the table in the last few years? What have been some of his biggest lessons on when to sell? How does Sheel evaluate the flood of capital into emerging markets in the bull market? What happens now? Fintech is also experiencing the same challenging time, how does Sheel assess what is happening in the fintech financing market today? 4. Building a Fund: Lessons, Mistakes and Advice Scaling to $225M: What are the single biggest mistakes Sheel and Jake have made in the fun scaling? How has it impacted their mindset? What does Sheel know now about fund management that he wishes he had known at the beginning? What advice does Sheel give to emerging managers today, raising their first and second funds?

14 Jul 202349min

Kevin Egan is the Global Head of Enterprise Sales at Atlassian and brings more than 25 years of enterprise sales experience and leadership to the company. Prior to his current role, Kevin served as the Vice President of North America Sales at both Slack and Dropbox and has held various senior sales leadership positions at Salesforce. In Todays Episode With Kevin Egan We Discuss: 1. The Makings of a Truly Great Enterprise Sales Leader: How did Kevin first make his way into the world of enterprise sales? What does Kevin know now that he wishes he had known when he entered sales? What advice would Kevin give to a new sales leader today starting a new role? 2. The Sales Playbook: How does Kevin define "the sales playbook"? Does the founder have to be the one to create the sales playbook When is the right time to hire your first salespeople? Should they be senior or junior first? What are the different types of reps to hire in the early days? Should you hire two at a time? 3. PLG vs Enterprise: Does Kevin believe it is possible to run both PLG and enterprise playbook at the same time? How does one know when they are ready to scale from PLG into enterprise? What are the signs? What do companies need to change in the way their sales team, is structured to make the transition from PMG to enterprise sales? What are the single biggest mistakes Kevin sees founders make in the scaling from PLG to enterprise? 4. Hiring the Sales Team: What non-obvious characteristics and attitudes should we look for in sales reps? How does Kevin structure the hiring process for all new additions to sales and revenue teams? What makes good PLG sales leaders? How are they different from enterprise sales leaders? What questions and case studies are most revealing for you in identifying them? What have been some of Kevin's biggest lessons on comp structure for these early rep hires? 5. Making the Machine Work: How does Kevin build trust with his early sales rep hires? What works? What does not? How does Kevin balance hitting the quarterly revenue target with longer-term pipeline strategy? How does Kevin manage when a quarter is missed? What is the right approach? How does Kevin approach post-mortems and deal reviews? How often? What do the best entail?

12 Jul 202336min

Simon Sinek is an optimist and author, as we discuss in the show today. Simon is best known for his TED Talk on the concept of WHY (62M views), and his video on millennials in the workplace (80M views in 7 days). Simon is also a bestselling author including global bestseller Start with WHY, Leaders Eat Last and The Infinite Game. In addition, Simon is the founder of The Optimism Company, a leadership learning and development company, and he publishes other inspiring thinkers and doers through his publishing partnership with Penguin Random House called Optimism Press. In Today's Discussion with Simon Sinek We Discuss: 1. The Makings of Simon Sinek: In what ways does Simon believe that his parents and upbringing shaped who he is today? What does Simon want to be when he grows up? What was the catalytic moment to the "Simon Sinek brand"? When was that big break moment? 2. Identity: Simon has said before, "I define myself by who I am and not what I do". Is it wrong to define yourself by what you do? What do you do if you do not know who you are? What do you do if you do not like the answers to who you are? Is it possible to change who you are? What does that process look like? What is Simon's biggest advice to those looking to find a greater sense of self and identity? 3. Trust: Does Simon start relationships with inherent trust and it is there to be lost or no trust and it is there to be gained over time? When has someone broken Simon's trust? How did it impact how he approaches trust today? In the case of cheating in a relationship, does Simon believe it is possible to regain trust over time? Simon has said before, "trust is built on telling the truth". Does it ever make sense or is even right to tell a little white lie in a relationship? 4. Creating Safe Spaces: How can we create safe spaces for our partners to be their full selves? Does this differ professionally and personally? What are the biggest mistakes people make in building safe spaces? 5. Listening: What does great listening in a relationship mean? How can we do it better? Often people jump from listening to solution mode, is that wrong? Why does Simon have a rule of “no crying alone”. What does it do and how is it productive? When was the last time Simon cried? 6. Simon Sinek: AMA: What is success to you? Can one be “successful” and unhappy? What is the difference between happiness and joy?

10 Jul 202352min

Douwe Kiela is the CEO of Contextual AI, building the contextual language model to power the future of businesses. Last month Contextual closed a $20M funding round including Bain Capital, Sarah Guo, Elad Gil and 20VC. He is also an Adjunct Professor in Symbolic Systems at Stanford University. Previously, he was the Head of Research at Hugging Face, and before that a Research Scientist at Facebook AI Research. In Today's Episode with Douwe Kiela We Discuss: 1. Founding a Foundational Model Company in 2023: How did Douwe make his way into the world of AI and ML over a decade ago? What are some of his biggest lessons from his time working with Yann LeCun and Meta? How does Douwe's background in philosophy help him in AI today? 2. Foundational Model Providers: Challenges and Alternatives: What are the biggest problems with the existing foundational data models? Will there be one to rule them all? How does the landscape play out? Why does Douwe believe OpenAI's data acquisition strategy has been the best? 3. Data Models: Size and Structure: Why does Douwe believe it is naive to think the open approach will beat the closed approach? What are the biggest downsides to the open approach? Does the size of data model matter today? What matters more? How important is access to proprietary data? Are VCs naive to turn down founders due to a lack of access to proprietary data? 4. Regulation and the World Around Us: How does Douwe expect the regulatory landscape to play out around AI? Why is Europe the worst when it comes to regulation? Will this be different this time? How does Douwe analyse Elon's petition to pause the development of AI for 6 months? Do founders building AI companies have to be in the valley?

30 Jun 202342min

Jennifer Hyman is the Co-Founder and CEO of Rent the Runway, the world’s first and largest shared designer closet. Under Jennifer’s leadership, RTR has made history by being the first company to go public with a female founder/CEO, COO, and CFO. Jennifer serves on the Board of The Estée Lauder Companies and Zalando, and also is a Founding Member of the NYSE Board Advisory Council, a Member of the Women.nyc Advisory Board and a Member of the Launch with GS Advisory Council for Goldman Sachs. In Today's Episode with Jennifer Hyman We Discuss: 1. The 14-Year Overnight Success: Scaling Rent The Runway To IPO: What was the a-ha founding moment for Jennifer with RTR? What does Jenn know now that she wishes she had known at the beginning? Does Jenn believe that naivete is good or not when starting a business? 2. Building the Best Team: What have been Jenn's single biggest lessons when it comes to acquiring the best talent? What have been Jenn's biggest hiring mistakes over the years? How does Jenn approach the interview process? Why does Jenn not focus on their professional career and achievements? What questions does she ask? What does Jenn believe are the single biggest mistakes founders make when building their teams? 3. Building the Business for IPO and Beyond: Why does Jenn wish she had run RTR as a private company in the same way she does now as a public company? How does the way you run the company differ? What about the unit economics of RTR suggesting it is a fundamentally better business than apparel competitors? How have their margin profiles changed over time? Why does Wall St not love RTR? What is required for that to change? Why does Jenn believe the street is wrong on how they analyse RTR? 4. Boards 101: Leading and Learning from Estee Lauder: What are Jenn's biggest lessons to founders on how to manage boards successfully? What have been 1-2 of Jenn's biggest lessons from being on the Estee Lauder board? What do the best board members do? What do the worst board members do?

28 Jun 202340min