Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds focused on SaaS. In the past, Jason has led investments in Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few. Prior to SaaStr, Jason was an entrepreneur, selling EchoSign to Adobe for $100M where it is now a $250M ARR product.

In Today's Episode with Jason Lemkin We Discuss:

1. WTF is Happening At Seed Right Now:

• Why does Jason believe seed is more active than ever?
• Is the pricing of seed rounds impacted since the downturn?
• Why does Jason believe it is not only not the end of party rounds but just the beginning of them?
• Why does Jason believe you cannot fail if you have $1M in ARR and an amazing founder?
• Why does Jason believe that seed investors cannot participate in "hot seed rounds" anymore?

2. Is Series A a Dead Zone:

• How does Jason analyze the Series A and B environment today?
• What has changed in what investors expect and want to see in potential Series A and B investments?
• What happens to the many companies who raised pre-emptive Series As and have 10 years of runway but no product-market fit?
• Why does Jason believe founders should offer to give the money back when it is not working?
• What happens to the Series A and B market in the next 18 months? When does it come back?

3. Growth: People are Too Negative!

• Why does Jason believe that growth is more active than many are giving credit for?
• What are the ARR benchmarks required to get a good growth round term sheet today?
• Why does Jason believe that VC DD is a load of BS?
• Why does Jason believe that every VC has fraud in their portfolio? Will they come out?

4. Ring That Bell: IPOs and M&A:

• Why does Jason believe 2024 will be an amazing year for IPOs?
• Why does much of the IPO market rely on Stripe and Databricks?
• What is needed for an amazing 2024 IPO market?
• How does Jason evaluate the M&A market in 2024? Will regulation get in the way?

5. Jason Lemkin: AMA:

• Why does Jason Lemkin believe this generation of workers will never work hard again?
• What is the only way for seed funds to make money investing in serial entrepreneurs?
• What does Jason know now that he wishes he had known when he started investing?

Vinod Khosla is the Founder of Khosla Ventures, one of the leading venture firms of the last decade with investments in OpenAI, Stripe, DoorDash, Commonwealth Fusion Systems and many more. Prior to founding Khosla, Vinod was a co-founder of Daisy Systems and founding CEO of Sun Microsystems.

In Today's Episode with Vinod Khosla We Discuss:

1. The State of AI Today:

• Does Vinod believe we are in a bubble or is the excitement justified based on technological development?
• What are the single biggest lessons that Vinod has from prior bubbles?
• What is different about this time? What is Vinod concerned about with this AI bubble?

2. The Future of Healthcare and Music:

• How does Vinod evaluate the impact AI will have on the future of healthcare?
• How does Vinod analyse the impact AI will have on the future of music and content creation?
• Does Vinod believe that humans will resist these advancements?
• Who will be the laggards, slow to embrace it and who will be the early adopters?

3. Solving Income Inequality:

• Does Vinod believe AI does more to harm or to hurt income inequality?
• What mechanisms can be put in place to ensure that AI does not further concentrate wealth into the hands of the few?
• Does Vinod believe in universal basic income? What does everyone get wrong with UBI?

4. The Future of Energy, Climate and Politics:

• Why is forcing non-economic solutions the wrong approach to climate? What is the right approach?
• Why is Vinod so bullish on fusion and geothermal? How does fusion bankrupt entire industries?
• How does the advancements in energy and resource creation change global politics?
• Does Vinod believe Larry Summers was right; "China is a prison, Japan is a nursing home and Europe is a museum"?

5. Vinod Khosla: AMA:

• What is Vinod's single biggest investing miss?
• What does Vinod know now that he wishes he had known when he started investing?
• Why did the Taylor Swift concert have such a profound impact on him?
• What was Marc Andreesen like when he backed him with Netscape in 1996?

Ilir Sela is the Founder and CEO of Slice, the all-in-one ordering and marketing tech platform for local pizzerias. Through its partnerships, Slice has driven over $1B in earnings for over 18,000 independent pizzerias nationwide. Fun fact, Slice is also one of the largest employers in Macedonia and at one point, employed so many people there, they had to start their own school to train more people. Before Slice, Ilir started Nerd Force and sold it in 2008. Huge thanks to Jeff Richards (GGV) and Ben Sun (Primary) for some amazing questions today.

In Today's Discussion with Ilir Sela We Discuss:

1. From Macedonia to the Bright Lights of NYC and Bentley Buying:

• How Ilir made his way into the world of startups having grown up in Macedonia?
• How did his less affluent upbringing impact his approach to company building?
• How does Ilir think about the importance of money? How did he come to buy a Bentley?
• What does Ilir know now that he wishes he had known when he started?

2. Why Bootstrapped Was Best & The Decision to Fundraise:

• Why did Ilir scale the business to $4M in revenue without ever fundraising?
• What does Ilir believe are the benefits of scaling businesses with less money?
• What would Ilir have done differently had he raised money earlier?
• What advice does Ilir have for founders who see competitors raising more money than them?

3. Why Delegation is BS and Your Upbringing F***** You Up:

• Why does Ilir believe that much of our upbringing can instill principles which make us a worse leader?
• Why does Ilir believe it is BS to hire great people and get out of the way?
• What are the single biggest mistakes Ilir sees founders make in company scaling?
• What have been some of Ilir's biggest lessons in talent acquisition?

4. Decision-Making 101:

• How does Ilir analyze his decision-making framework today?
• Where does he need to improve as a leader today? What does he need to do to get there?
• What has been the single best decision he made with Slice? What did he learn from it?
• What has been the worst decision he has made in the scaling process? How did that change his mindset?

Lori Jimenez is the Chief Revenue Officer at WorkRamp where she is responsible for sales, customer success, solutions engineering, sales development, and revenue operations. Over her 25-year career, Lori has a track record of scaling high-growth GTM teams at companies including Google, TripActions/Navan, Facebook, and Box.

In Today's Episode with Lori Jimenez We Discuss:

1. From a First Sales Job at 15 Years Old to Leading Sales Teams at Google and Facebook:

• How Lori made her foray into the world of sales at the age of 15?
• What are 1-2 of Lori's biggest takeaways from her time at Google, Facebook and Box?
• What does Lori know now that she wishes she had known at the start of her career in sales?

2. The Sales Playbook: What, When and How:

• How does Lori define the "sales playbook"? What is it not?
• Should the founder be the one to create the sales playbook?
• When is the right time for founders to make their first sales hires?
• What is the right profile for the first sales hires?
• Should founders hire 2 sales reps at a time? What are the pros and cons?

3. The Hiring Process: Building the Sales Team:

• How does Lori structure the hiring process for all new sales hires?
• What are the must-ask questions to ask in every sales hiring meeting?
• What are the biggest red flags founders should look for when hiring for sales?
• What are Lori's biggest lessons on how to navigate compensation discussions with potential sales hires?
• What are Lori's biggest lessons on what title negotiation says about a candidate?
• What are the single biggest mistakes founders make when hiring for sales teams?

4. Scaling the Machine: Bringing the Dollars In:

• How does Lori approach discounting? When is the right time to do it?
• Is old-school enterprise sales and entertaining dead? How has it changed?
• How does Lori structure deal reviews? What is a good vs a bad reason to lose a deal?
• How does Lori approach multi-year deals? What is good? What is bad?

Marcelo Claure is the Founder & CEO of Claure Group, a multi-billion-dollar global investment firm. He is the Executive Chairman and Managing Partner of Bicycle Capital, a $500M Latin America-focused growth equity fund, and was appointed Chairman in Latin America of SHEIN, the global #1 on-demand fashion company in the world. Claure was also the CEO of SoftBank Group International where he launched SoftBank’s $8B Latin America Funds, and had direct oversight for SoftBank's operating companies. As an entrepreneur, Marcelo built Brightstar from a small local distributor to the world’s largest global wireless distribution and services company. In addition, Claure led the turnaround of US wireless telecommunications company Sprint and helped orchestrate its US$195 billion merger with T-Mobile.

Shu Nyatta is the founder of Bicycle Capital. Before Bicycle, Shu was most recently a Managing Partner at SoftBank Group International, where he launched and managed two separate funds - the SoftBank Latin America Fund and the Opportunity Fund for early-stage investments in US-based founders-of-color. In the first part of his SoftBank career, Shu was a founding Partner of SoftBank's Vision Fund. Several companies have retained him on their boards as an independent board member following his departure from SoftBank, including Lemonade (NYSE: LMND), Kavak and Tribal Credit. Shu also serves on the board of Endeavor Global - the leading global community of, by and for high-impact entrepreneurs.

In Today's Episode Featuring Bicycle Capital We Discuss:

1. From Deploying $10BN at Softbank to Founding Bicycle Capital:

• What was the founding moment for Marcelo and Shu in the founding of Bicycle?
• What does Shu believe is Marcelo's superpower? How has working with Marcelo changed the way he thinks?
• Why does Marcelo believe that he is not a good investor? How does Shu make him better, specifically?

2. Lessons from Investing $10BN at Softbank:

• What are 1-2 of the biggest lessons from investing $10BN over the last few years at Softbank?
• How did missing OpenAI and Nubank impact how Shu and Marcelo think and invest today?
• Why was losing $150M on Softbank's FTX investment, the biggest lesson of Marcelo's career?
• What are Marcelo and Shu doing differently at Bicycle, having seen how it went at Softbank?

3. The Venture World is Changing:

• Why do Marcelo and Shu believe the world of venture is changing? How is it changing most?
• Why are founders going directly to LPs to raise rounds today, over going to VCs?
• Do Marcelo and Shu believe that many VCs provide value?
• Who will win in the next 10 years of venture? Who will lose?
• Why do Marcelo and Shu believe you should not invest in founders that do not take your advice?
• Do Marcelo and Shu agree with the statement that "the best founders do not need your help"?

4. LATAM is Under Construction: It is Time to Build:

• What are the two reasons that the next decade will be the best ever for LATAM?
• What are the biggest misconceptions about the LATAM tech market?
• How do Marcelo and Shu answer the question of the lack of liquidity available with few M&A deals taking place and very few LATAM companies listing on the NASDAQ?
• How do Marcelo and Shu evaluate the withdrawal of foreign capital from LATAM tech markets? Is it good or bad? Have a load of US funds lost money on early-stage LATAM deals?

Stephane Kurgan is widely considered one of the best operators in Europe. During his tenure as COO @ King, King went from $65m to $2.4B in bookings, from 100 to 2,400 employees, and did a $7B IPO before being acquired by Activision Blizzard. Prior to joining King, Stephane served as CFO of Tideway Ltd. (acquired by BMC Software) and was the co-founder and CEO of Digital Reserve. Today, Stephane serves as a Venture Partner at Index Ventures, one of the leading venture firms of the last decade and more recently as an executive advisor at Technology Crossover Ventures.

In Today's Episode with Stephane Kurgan We Discuss:

1. From Belgium Boy to Europe's Leading Operator:

• How a CD Rom company was the starting place for one of Europe's best executives?
• What does Steph believe he is running away from?
• What does Steph know now that he wishes he had known when he started?

2. Four Criteria of Truly Great Leaders:

• What four traits do all truly special leaders have?
• What are the 1-2 that are the hardest to find in great leaders today?
• Why does Steph believe that even the best leaders are wrong 40% of the time?
• How does Steph approach decision-making? How has it changed over time?
• What is the most toxic element of decisions within companies today?
• When does Steph change plan because a decision is wrong vs stick to it?

3. Speed of Execution and Mission Statements:

• How important does Steph believe speed of execution is today?
• What are the elements that one can go fast on vs go slow and be very deliberate on?
• What elements has Steph gone fast on in the past that led to a mistake? How would he have changed his approach with the benefit of hindsight?
• Why does Steph believe that mission statements have different value at different company stages?
• What is Steph's biggest advice to founders on creating mission statements?

4. Delivering Feedback and Maintaining Trust:

• What are 1-2 of Steph's biggest lessons when it comes to delivering feedback well?
• What are the biggest mistakes founders make when delivering feedback today?
• Can trust be regained once lost? How?
• Does Steph start from a position of full trust or is it gained gradually over time?

Sri Batchu currently leads Growth at Ramp. He previously led Growth Strategy and Operations at Instacart where he also helped grow their Ads business. Prior to that, he was one of the first 50 employees at Opendoor where he built, scaled, and managed a variety of business teams including Analytics, Sales, and Pricing.  During his time, the company grew from $100M to $5B+ revenue and to 1500+ people.  He started his career in management consulting at McKinsey and also held various investing roles including in private equity at Bain Capital. 

In Today's Episode with Sri Batchu We Discuss:

1. From Harvard to Private Equity to Leading the Best Growth Teams:

• How did Sri make his way into the world of growth with Instacart and Opendoor?
• What are 1-2 of his biggest takeaways from his time at Instacart? How did it change his approach and mindset towards growth?
• How did Zilllow burn themselves by buying homes? What did that teach Sri about hitting metrics and goal setting in growth teams?

2. Growth Teams Should Fail and Fail Fast:

• What is the right ratio of success to failure within growth teams?
• What are specific ways that growth teams can increase the speed with which they fail?
• How are the best post-mortems run? Who joins them? Who leads the agenda?
• What are Sri's biggest lessons on how to set the right goals?
• Where do so many growth teams go wrong with the North Star that they set for themselves?

3. Building the Bench: Hiring a Growth Team:

• When is the right time to make your first growth hires?
• What profile should your first growth hires be?
• How should one structure the interview process when hiring growth teams?
• What is the first question Sri asks all new hires?
• Why does Sri believe you have to hire slowly?
• Should candidates do case studies as part of the process, if so, on a new company or on the company they are interviewing for?

4. When Operators Become Investors:

• Why does Sri believe the best investors of the next 10 years will be operators?
• Why does Sri believe that operators can do due diligence to a higher level than traditional VCs?
• Why does Sri believe that investors should not take cold emails?
• Why does Sri believe that it is not wrong for an investor to hire from their portfolio companies?
• What does Sri believe the future of venture holds over the next 10 years?

Adam Mosseri is the Head of Instagram, where he is responsible for overseeing the engineering, product, and business teams and leading Meta’s efforts on creators and Reels. Adam has been at Meta for more than fifteen years. He started at Meta as a designer for Facebook's mobile app before moving to product management, where he led the Facebook News Feed product and engineering teams, and served as the Head of Facebook News Feed. Adam began his career founding a design consultancy focused on graphic, interaction, and exhibition design before joining TokBox as the company’s first designer.

In Today's Discussion with Adam Mosseri We Discuss:

1. From Designer to Product Leader to Instagram CEO:

• What did Adam learn from his first job bartending? How did it impact his approach to customer support and research?
• What are the top 1-2 pieces of advice Adam would give to someone wanting to make the move from individual contributor to leader?
• If Adam was "not amazing at anything", what did he do that enabled him to rise above the rest and become CEO of Instagram?
• What have been 1-2 of the biggest lessons from working with Mark Zuckerberg for 15 years?

2. A Deep Dive on the Wild Times as Instagram CEO:

• What has been Adam's single biggest mistake as CEO of Instagram?
• What does Adam believe is the least known feature within Instagram that has made them successful?
• What does Adam believe has been the biggest product decision he has made as CEO?
• Why does Adam believe that Instagram is too complicated as a product?
• Who does Adam believe is the most formidable competitor to Instagram?
• Was Instagram Reels a simple copy of TikTok? What have Instagram learned from TikTok?
• How does Adam respond to the statement that Instagram is a "copy-cat machine" and lacks innovaton?

3. Threads: The Journey from 0-100M Users in Three Days:

• Did Adam and the team expect the response they got to Threads?
• Why did they decide to break Threads out into a separate app?
• What went into bootstrapping the Threads friendship and interest graph?
• What was the Threads influencer activation strategy? What worked? What did not? Did they pay influencers? How did they choose which verticals to focus on?
• What is Adam's core focus with Threads today?
• How is the team analysing and measuring retention? What are their goals?
• What are the 1-2 core reasons why Threads would not work? How do they aim to prevent them?
• In 12 months, where will Threads be?

4. The Future of Consumer Social: What Happens Now?

• Does Adam believe we have seen the transition from the social graph to the interest graph? Is it that binary?
• Is it possible to have both the interest and the friendship graph all in one app?
• How does the monetization potential differ when comparing Threads (text) to Instagram (visual)?
• How important is it for the next consumer social platforms to have stars that are native to their platform (Mr Beast on Youtube, D'Amelio on TikTok etc.)

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?

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?

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?

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?

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?

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?

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?

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?

Akin Babayigit is a serial entrepreneur and an active angel investor. He is currently the Founder and COO of Tripledot Studios, one of the fastest-growing mobile gaming companies in the world, which was recently valued at over $1.4BN. In just 4 years, Tripledot grew to generate several hundred million dollars per year in revenue and currently entertains over 50 million people every month. Tripledot was recently named as the #1 fastest-growing European company by FT, as well as being named as the fastest-growing Tech business in the UK, in the annual “UK Tech Awards”.

In Today's Episode with Akin Babayigit We Discuss:

Entry into the World of Startups and Gaming:

• How Akin made his way from Turkey to HBS and founding a unicorn in Tripledot?
• How did the lack of a father figure impact Akin's approach to parenting?
• What are 1-2 of Akin's biggest takeaways from his time at Facebook, Skype and King.com?
• What advice would Akin give to all new joiners at a company today?

90% of Startup Advice is Total BS:

1. BS Myth #1: "You have to be passionate about your domain". Why does Akin disagree with this? If you do not have passion for the domain, what do you have to have?
2. BS Myth #2: "You have to be solving a real problem". Why does Akin disagree with this mantra? If you are not solving a real problem, what should you be solving?
3. BS Myth #3: "When you do a startup, your life will suck for a long period of time". Why does Akin strongly disagree with this? Does it get easier over time? What does Akin advise founders to make the earlier days easier?
4. BS Myth #4: "Focus is everything. You should focus on a single thing and only do that." Why does Akin believe that focus can be dangerous? How should founders know when to pivot vs when to keep going?
5. BS Myth #5: "Mission and vision statements are so important." Why does Akin believe that the majority of mission statements are BS? Is it worth having them at all?
6. BS Myth #6: "You should hire people with domain experience." Why does Akin believe you should hire people who do not have domain experience? What does Akin look for in these candidates? What have been his biggest hiring mistakes? How has his hiring changed over time?
7. BS Myth #7: "Speed is the most important thing." Why does Akin believe that speed can be dangerous? When is it right to go fast vs go slow?
8. BS Myth #8: "Valuations matter and you should optimize." Why does Akin believe that valuations do not matter in the long run? How should founders approach the valuation discussion with this in mind?

Rob Go is a co-founder and Partner at NextView, one of the leading seed firms of the last decade with a portfolio including Attentive, Devoted Health, Whoop, and Grove Collaborative. Prior to co-founding NextView, Rob was an investor at Spark Capital and held product and product marketing roles at Ebay. He began his career as a consultant at The Parthenon Group.

In Today's Episode with Rob Go We Discuss:

1. Entry into the World of Venture:

• How a cold call from a VC firm led to Rob entering the world of venture?
• Why does Rob believe venture is a young person's game?
• What does Rob know now that he wishes he had known when started in venture?

2. Preparing Docs for a Fundraise:

• What docs should fund managers have ready before they start the raise?
• How should they structure their data room?
• Where do the majority of LPs spend their time, document-wise?
• What are the single biggest mistakes emerging managers make preparing docs for a raise?

3. Meeting Your First LPs:

• What is the best way for emerging managers to meet LPs for the first time?
• Should they send the deck before or after the meeting?
• What questions should emerging managers ask to qualify LPs in or out of a meeting?
• What are some clear early signs that a first meeting went well?

4. Closing LPs: The Tips and Tricks:

• How important is it for a fund to have an anchor?
• How much of a fund should the anchor be?
• Are there different qualities of anchor LPs?
• Should managers ever sell part of their GP or give an LP part of the carry?
• What can managers do to enforce a sense of urgency to get LPs over the line?
• What are signs that an LP will not invest in the fund without rejecting you yet?
• Should emerging managers impose a minimum check size on new LPs?

Gina Gotthilf is a Co-Founder and COO at Latitud, an a16z-backed platform supporting the next generation of iconic tech startups in Latin America through digital products, a community and fund. Previously, Gina led growth and marketing at Duolingo from 3 to 200 million users via organic strategies and was part of the executive team. She also worked on the Mike Bloomberg presidential campaign, helping oversee the creation of digital ad campaigns at a historical budget, and led growth and community for Tumblr in Latin America.

In Today's Discussion with Gina Gotthilf We Discuss:

Entry into the World of Growth:

• How Gina went from working on a farm to leading growth for Tumblr in LATAM?
• What are 1-2 of Gina's biggest takeaways from her time leading growth for Duolingo?
• What does Gina know now that she wishes she had known when she entered the world of growth?

15 Top Tips and Secrets to Being Featured in the Best Publications:

• What is the best way to get in touch with journalists? What mistakes do founders have when they reach out to journalists?
• Should founders get in touch with more than one journalist at a publication?
• Should founders be explicit about the embargos they have on a story? Should they stick to them?
• Should founders be more wary of being published in a publication with a paywall?
• What materials should they send to journalists to get their attention?
• Should founders send press releases in early messages to journalists?
• How can founders control in some way what the journalist will ultimately publish?
• How long before the company wants the piece to come out, should they reach out to journalists?
• How can founders create FOMO when trying to get journalists to write their story?
• How can founders create social validity with journalists, when they are a small company?
• Once published, what should the distribution strategy look like?
• How can you get people you know to like and share content you are featured in?
• What are the top tips and tricks to get people to share content with you in?
• Should PR and Comms be an ongoing effort or static projects with news stories?
• What are the single biggest mistakes founders make in getting their company in the press?

Alex Lebrun is the Co-Founder and CEO of Nabla, an AI assistant for doctors. Prior to Nabla, he led engineering at Facebook AI Research. Alex founded Wit.ai, an AI platform that makes it easy to build apps that understand natural human language. Wit.ai was acquired by Facebook in 2015. Prior to Wit, Alex was the Founder and CEO of VirtuOz, the world pioneer in customer service chatbots, acquired by Nuance Communications in 2013.

In Today's Episode with Alex Lebrun We Discuss:

1. Third Time Lucky and Lessons from Zuckerberg:

• How did Alex make his way into the world of startups with the founding of his first company?
• What worked with Alex's prior companies that he has taken with him to Nabla? What did not work that he has left behind?
• What were the single biggest takeaways for Alex from working with Mark Zuckerberg? How does Mark prepare for meetings? How does Mark negotiate so well?

2. Open vs Closed:

• Why does Alex believe the winning AI models will always be open?
• Why are open models not as transparent as people think they are?
• What are the biggest downsides to both open and closed models?
• Does Alex agree with Emad @ Stability that we will have "national data sets"?

3. Incumbent vs Startup:

• Who wins in the AI race; startups or incumbents?
• How important is access to proprietary data in winning in AI today?
• How does Alex respond to many VCs who suggest so many AI startups are merely "a thin layer on top of a foundational model"? Is that a fair critique?
• Which startups are best placed to challenge incumbents? Which incumbents have been most impressive in adopting AI into existing product suites?

4. Models 101: Size, Quality, Switching Costs:

• Why will the best companies switch the models that they use often?
• Will any models in action today be used in a year?
• How important is the size of the model? How will this change with time?
• In what way is new EU regulation around models going to harm European AI companies?

5. Location Matters: Who Wins:

• When looking at China, US and Europe, who is best placed to win the AI war?
• What are the biggest challenges Europe and China face?
• Why is the US best placed to win the AI race? What does it have to overcome first?
• If Alex were a politician, what would he do to ensure his country were best positioned?

Noah Weiss is the Chief Product Officer of Slack, overseeing the product team’s strategy and development. Over his seven years at Slack, Noah has led various parts of the product organization, including the self-service SMB business and product-led growth; the Virtual HQ team that launched huddles and clips; and the search and machine learning teams. Prior to Slack, Noah served as SVP of Product and Analytics at Foursquare. He started his career at Google leading the structured data search team and working on display ads.

In Today's Episode with Noah Weiss We Discuss:

1.) Entry into Product and Road to Slack CPO:

• How did Noah make his first foray into the world of product with Google?
• What are 1-2 of his single biggest takeaways from his time with Google and Foursquare?
• What model did Noah learn at Google that he applies to product today?

2.) Product 101: The Foundations:

• Is product more art or science? If Noah were to put a number on it what would it be?
• What are product principles? What makes good vs bad product principles?
• What are the biggest mistakes that founders make when instilling product principles?
• Does Noah believe with Gustav Soderstrom, "talk is cheap and so we should do more of it"?

3.) How to Master Product-Led-Growth:

• What are some of Noah's biggest lessons on how to master PLG?
• What are the biggest mistakes Noah sees early stage founders make today when going for the PLG approach? How does he advise them?
• When is the right time to move into enterprise? What needs to change?
• How do you change who you build product for? The buyer or the user?
• Why does Noah believe product speed will always be the most important thing in product?

4.) The Internals of Slack:

• How does Slack do post-mortems today? Who comes? Who sets the agenda? How has this changed in a world of remote? What does it take to do them well?
• How do Slack do product testing pre-launch of new products? Do they know when something is going to be a hit? What did they think would be a massive hit that turned into a flop?
• What does Noah believe is the biggest near death product experience for Slack? What happened? How did they get through it?
• Why do Slack buy other companies? How do they think through the decision of buy vs build?
• When do acquisitions work? When do they not work?

Rishi Sunak is the Prime Minister of the United Kingdom. He was previously appointed Chancellor of the Exchequer from 13 February 2020 to 5 July 2022. He was Chief Secretary to the Treasury from 24 July 2019 to 13 February 2020, and Parliamentary Under Secretary of State at the Ministry of Housing, Communities and Local Government from 9 January 2018 to 24 July 2019. Before entering the world of politics, Rishi co-founded an investment firm.

In Today's Episode with Rishi Sunak We Discuss:

1. The United Kingdom: Open for AI: Open for Business

• Why does Rishi believe the UK is best placed to lead the way for innovation in AI?
• What can the government do to ensure the public and private sectors work together most efficiently?
• Why has Rishi created an entirely new division just for this? How does this change how decisions for AI and technology are made?

2. $100M Funding: The Largest Government Funding in the World:

• Why did Rishi decide to allocate the largest pool of capital of any nation toward AI safety?
• What is the strategy for the $100M? How will it be invested? Who will manage it?
• What are the challenges and opportunities in setting up this $100M funding program?

3. Education: Attracting the Best in the World:

• What has Rishi done to ensure the best talent in the world, wants to and can work in the UK?
• What new initiative has Rishi put in place to ensure the world's brightest students can freely move to and work in the UK?
• What can be done to ensure the UK continues to foster the same level of homegrown talent that we always have done? What can we do to improve our current education system for AI even further?
• Why does Rishi believe one of the greatest opportunities for AI lies in education and teaching?

4. Making Regulation Work Effectively:

• How does Rishi think about creating regulation which is both effective and not prohibitive?
• What can we do to create a government that moves at the speed of business?
• What does Rishi believe are the biggest mistakes made in regulatory provisions? What are we doing to avoid them with AI in the UK?

Larry Summers is the Former Treasury Secretary and one of America's leading economists. In addition to serving as 71st Secretary of  the Treasury in the Clinton Administration, Dr. Summers served as Director of the White House National Economic Council in the Obama Administration, as President of Harvard University, and as the Chief Economist of the World Bank. Huge thanks to Sarah Cannon for the intro to Larry today.

In Today's Episode with Larry Summers We Discuss:

1. The Journey to Being One of the World's Leading Economists:

• How Larry's mother and father both being economists shaped his early thinking as an economist?
• How did Larry's parenting teach his children economics at an early age?
• What does Larry know now that he wishes he had known when he entered the workforce?

2. How to Get the US Out of Debt:

• What would Larry do to save the US economy today?
• What can be done to increase revenues for the US economy?
• Why does Larry believe carried interest should be taxed as income tax?
• Why does Larry believe we need more billionaires? How would he tax them more efficiently?
• Why does Larry believe cutting taxes is indefensible?
• What can be done to reduce inflation without massively hurting the poorest in society?

3. The World Around Us:

• What does Larry mean when he says, "Europe is a museum, China is a jail and Bitcoin is an experiement"?
• Why does Larry believe the next 5 years will be difficult for China?
• Why does Larry believe the next 5 years will be challenging for Europe?
• Which nation is Larry most confident about when projecting forward for the next 5-10 years?

4. Politics and a Trump Administration:

• How does Larry reflect on the role of Biden on the US economy and state of inflation?
• Would a Trump administration be better or worse for the US economy?
• What are the chances of Trump beating Biden in the next election?
• What would Larry most like to change about the US political system?

Orlando Bravo is a Founder and Managing Partner of Thoma Bravo. He led Thoma Bravo’s early entry into software buyouts and built the firm into one of the top private equity firms in the world. 

Tobi Lütke is the CEO and Co-Founder of Shopify, the powerhouse company allowing anyone to start and grow their e-commerce business.

Dara Khosrowshahi is the CEO of Uber, where he has managed the company’s business in more than 70 countries around the world since 2017.

Parker Conrad is the Founder & CEO @ Rippling, the company that lets you easily manage your employees’ payroll, benefits, expenses, devices, apps & more—in one place.

Jamie Siminoff is the Founder and Chief Inventor @ Ring, with Ring Jamie, created the world’s first Wi-Fi video doorbell while working in his garage in 2011. The company sold to Amazon for $1BN.

Martín Escobari is Co-President, Managing Director and Head of General Atlantic’s business in Latin America. Martín is Chairman of the firm’s Investment Committee and also serves on the Management and Portfolio Committees.

Ariel Cohen is the Co-Founder and CEO @ Navan (formerly TripActions), the #1 travel management super-app used by over 8,000 companies.

Tarek Mansour is the Founder and CEO @ Kalshi, the first regulated exchange where you can trade directly on the outcome of events.

Brian Armstrong is the Co-Founder and CEO @ Coinbase, the easiest place to buy and sell cryptocurrency. Over the last 10 years, Brian has led Coinbase to today, a public company with over 3,500 employees and revenues of over $7.5BN in 2021.

Question of the Day:

What are the world's tech leaders running from?

Rich Liu is the CRO @ Everlaw and a unicorn GTM exec having scaled five multi-billion dollar tech unicorns across two IPOs, a successful acquisition, and numerous funding rounds. Prior to Everlaw, Rich architected the GTM motions for companies like Navan (TripActions), MuleSoft, and Meta (Facebook). As a result of his incredible success, Rich has been recognized as a 2021 Top 100 Global Sales Leader.

In Today's Episode with Rich Liu We Discuss:

1. Entry into the World of Sales:

• How Rich made his way from biochemistry into the world of sales?
• What is 1 takeaway from his time at Navan, Meta and Mulesoft that has shaped how he thinks about sales today?
• What does Rich know now that he wishes he had known when he entered the world of sales?

2. Sales Today: What is Happening?

• What are the biggest sales leaders saying today about price sensitivity and deal cycles?
• What has changed in the way companies buy software with the macro downturn?
• What do companies need to do to get deals over the line today?
• How do startups need to change the way they message to enterprises in order to sell today?
• How has the renewals process changed? What does this mean for customer success teams today?

3. PLG vs Enterprise: When and How?

• Is it possible to do both PLG and enterprise at the same time?
• Is it easier to start with enterprise and move to PLG or visa versa?
• How does the type of sales leader you need change dependent on the motion?
• When is the right time to move from founder-led sales to sales team?
• How does one know whether to hire a junior jack of all trades or a senior sales leader?

4. How To Hire The Best in Sales:

• How does Rich structure the hiring process for all new reps today?
• Does he use case studies to determine their depth and ability? Is the case study of the company they are interviewing at or a fresh company?
• What questions does Rich ask every candidate for a new role?
• What are some of the biggest red and green flags in how candidates talk in interviews?