Miki Kuusi is the CEO of Wolt and Head of DoorDash International. In 2014 Miki founded Wolt with a mission to turn the smartphone into a remote controller for life, starting with delivering your favorite restaurant food, to you at home. Today Wolt operates in 23 countries, across several different categories, has over 4,000 employees, and last year, Doordash made the move to join forces with Wolt in a deal worth a reported $8.1BN. Previously, Miki was the CEO of Slush, one of the leading tech and investor events in the world attended by more than 25,000 people annually.

In Today's Discussion with Miki Kuusi:

1.) Founding Slush and Wolt: An Entry into Startups:

• How did Miki come to found Wolt? What was that a-ha moment?
• Did Wolt have product-market-fit from Day 1? What was the turning point when they did?
• What does Miki know now that he wishes he had known when he started Wolt on Day 1?

2.) The Makings of a Truly Great Leader:

• How does Miki define "high performance" today in leadership?
• How does Miki think about what focus means in leadership? What is the hardest decision Miki has had to make when it comes to focusing the company? What did he learn from Ilkka @ Supercell?
• What does Miki believe is the KPI of success as the CEO? How does it change?
• What does Miki believe is the difference between good vs great leadership?
• What does Miki believe is the biggest sacrifice he has made as the CEO?

3.) Hiring a Team to Compete on a Global Stage:

• How does Miki use compensation to create a culture of ownership and accountability?
• Does Miki start from a position of trust and it is there to be lost or no trust and it is there to be gained?
• What is the difference between a team and a family in company building?
• What is the core difference between trust and safety in company building? Why does Miki always want to have trust but not want to have safety?
• What are the single biggest hiring mistakes that Miki has made? How has he learned from them?
• Why does Miki believe you do not want to hire people that have done it before but hire the people who have seen those people do it before?
• Why does Miki believe most companies are merely glorified recruiting operations?
• Does Miki believe that companies need to be as big as they have grown into, headcount-wise?

4.) Miki Kuusi: The Personal Journey

• What single day was the hardest day of the Wolt journey for Miki? How did it change him?
• Why does Miki believe that for their Series B, all-bar one VC turned them down?
• How does Miki assess his own relationship to risk and money today?
• Why is Miki an advocate for founders taking secondaries along the journey?
• What can Europe do to become a powerhouse in tech moving forward?
• Why did Miki decide to sell the company to Doordash? What is he most excited to learn from Tony Xu, Doordash Founder and CEO?

Items Mentioned in Today's Episode:

Miki's Favourite Book: The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers

Casey Winters is the Chief Product Officer at Eventbrite. Prior to Eventbrite, Casey led the growth product team at Pinterest. Before Pinterest, Casey started the marketing team at Grubhub and scaled Grubhub’s demand-side acquisition and retention strategies. 

Elena Verna is the Interim Head of Growth at Amplitude. Former exec @ Miro, Netlify, SurveyMonkey. Growth Advisor to companies including Krisp, MongoDB, Ledgy, Builder.io and SimilarWeb.

Kieran Flanagan is SVP Marketing at HubSpot, where he has helped the business grow internationally, move to a product-led business, quadrupled its marketing demand, and built out its media team, including the acquisition of ‘The Hustle.’

Andy Johns career started in growth at Facebook when the company scaled from 100M-500M active users. Since he has worked in some of the leading growth orgs at companies like Twitter, Quora and more recently at Wealthfront as Head of Growth and President.

Bangaly Kaba is the Director of Product Management @ Youtube. Prior to Youtube, Bangaly led the product growth and consumer product orgs at Instacart and before Instacart was Head of Growth @ Instagram, helping grow Instagram from 440M to > 1B monthly actives in 2.5yrs.

Ed Baker is a growth advisor to various startups including Lime, Zwift, Whoop, Crimson Education, GoPeer, and Playbook. Ed was the VP of Product and Growth at Uber from 2013-2017. Prior to Uber, Ed was the Head of International Growth at Facebook.

Adam Fishman was the Chief Product and Growth Offer @ Imperfect Foods. Before Imperfect, Adam was VP of Product and Growth @ Patreon, Before Patreon, Adam was the Head of Growth @ Lyft, Adam was the first growth and marketing employee hired and grew the team to 18 people.

In Today's Discussion on When To Hire a Head of Growth:

1.) When is the right time to hear your first growth hire?

2.) Is this hire a senior growth leader or a more junior growth engineer?

3.) What can early-stage startups do to entice senior growth leaders to their early-stage company?

4.) What data infrastructure should be in place prior to hiring your first growth hire?

5.) What does the optimal onboarding process look like for all growth hires?

6.) What can founders and CEOs do to set their growth hires up for success?

Jeffrey Katzenberg is an entertainment industry executive and entrepreneur, who throughout his career has repeatedly reshaped the media landscape. Jeffrey co-founded DreamWorks SKG, serving as CEO of DreamWorks Animation, which he grew into the world’s largest animation studio, known for Shrek, Kung Fu Panda, Madagascar and more. In 2016, DreamWorks Animation was sold to Comcast for $3.8 billion. Before founding DreamWorks, Jeffrey was Chairman of The Walt Disney Studios, where he took the studio from last place to first at the box office with hits like Three Men and a Baby, Pretty Woman, Father of the Bride and Sister Act. Most recently, Jeffrey co-founded WndrCo alongside Sujay Jaswa and has led WndrCo’s investments in Airtable, Frame.io, Quibi, Vise, Placer.ai, NexHealth, Deel, and ID.me.

Sujay Jaswa is one of Silicon Valley’s leading business innovators. At Dropbox, he created and led the company’s global business and finance organizations. Sujay and his teams raised over $1 billion, launched and scaled Dropbox’s products for businesses, created partnerships responsible for over 100 million users, executed some 20 acquisitions, and scaled the global business team from two to more than 500 employees in seven global offices. During this period, the company significantly scaled overall revenue from $12 million in 2010 to over $500 million run rate, Dropbox for Business revenue from $1 million to over $200mm run rate, and users from 15 million to 300 million. Most recently, Sujay Jaswa and Jeffrey Katzenberg co-founded WndrCo and Sujay has led WndrCo’s investments in Figma, 1Password, Databricks, Pango, Pilot, Rally, Zagat / The Infatuation, and other great companies.

In Today's Episode with Jeffrey Katzenberg and Sujay Jaswa:

1.) From Dreamworks and Dropbox to Venture with WndrCo:

• How did Jeffrey and Sujay both make their way into the world of venture from Dropbox and Dreamworks?
• What was Jeffrey's single biggest lesson from his time leading Dreamworks and being in Hollywood?
• What was Sujay's biggest takeaway from being at the helm as COO at Dropbox?

2.) Operating Experience is Irrelevant and Can Be Dangerous:

• Why does Sujay believe that operating experience is irrelevant?
• What are the single biggest mistakes that operator investors make when it comes to advising their founders?
• What do both Sujay and Jeffrey do to try and refresh their operating experience in real time?
• How did Quibi impact their willingness and desire to take large risk both investing and operating?

3.) Building Teams and Hiring People:

• What are the single biggest hiring mistakes Jeffrey and Sujay have made?
• What did Jeffrey mean when he said at Disney, “if you do not come in on Saturday, do not bother coming in on Sunday”.
• How do Jeffrey and Sujay feel about remote work? Why did it not work for them?
• What did Alfred Lin @ Sequoia teach Sujay about the question all managers need to ask themselves on questing whether they should let someone go?

4.) Silicon Valley: Dead and Entitled?

• Why does Jeffrey strongly disagree with the death of Silicon Valley?
• What will happen to the generation of companies that raised too much with no product-market fit?
• How will the mass layoffs in the valley change the valley as it is today?
• Does Sujay agree that millennials are the worst segment to hire from? Are they entitled?

Semil Shah is the Founder of Haystack, one of the leading pre-seed and seed firms of the last decade. Among Semil's portfolio include the likes of DoorDash ($DASH), Instacart, Hashicorp ($HCP), Opendoor ($OPEN), Figma (acquired by Adobe), Carta and many more exceptional companies. Semil's first fund is marked between a 30 and 40x fund, astonishing.

In Today's Episode with Semil Shah We Discuss:

1.) The Makings of Semil Shah:

• What is Semil running away from? What is he running towards?
• What does Semil know now that he wishes he had known when entering venture?
• What is Semil's biggest advice to managers raising their first funds now?

2.) Fund Sizing: Growing vs Staying Disciplined:

• Question from Hunter Walk: How does Semil determine the right size fund to raise with each fund
• Question from Satya Patel: Why have you resisted increasing AUM?
• In the last episode Semil mentioned a three-year deployment cycle for the fund, did he stick to it? What are the benefits and drawbacks?
• What investing mistakes did Semil make over the last 3 years that he wishes he had not made?  

3.) The Secret to Fundraising for a Fund:

• What is Semil's biggest advice to emerging managers on finding new LPs? What works?
• What materials do managers need to have in place for a new fundraise? Deck? Dataroom?
• What are the most common mistakes VCs make when pitching LPs their funds?
• How does Semil follow-up with potential LPs post-call? What works? What does not?
• How does Semil suggest creating a sense of urgency for LPs to commit to a fund?
• How does Semil feel about giving preferential terms to convince LPs to commit to the first close?

4.) The Current Landscape:

For VCs:

• How will the current landscape impact emerging managers' ability to raise?
• What advice would Semil give to them? Raise smaller?
• Kyle Harrison said on the show recently, “differentiation will kill 80% of venture firms, especially the so-so ones”. Does Semil agree? Who is set to struggle? Who is set to thrive in this environment?

For LPs:

• What does Semil think are the biggest mistakes LPs made over the last 2-3 years?
• How will they respond in this market cycle?
• If Semil were handed an endowment fund, how would he allocate today?
• Does Semil agree, we will see a denigration of venture returns to those of PE like multiples? Why?

For Founders:

• How does Semil advise founders on raising today when everyone says they are investing but very few really are?
• How does Semil advise founders on how to think about valuation inflection points with respect to raising capital?

Items Mentioned in Today's Episode:

Semil's Favourite Article: Master of Play

Semil's Most Recent Investment: Impart Security

Oana Olteanu is a Partner @ SignalFire where she focuses on enterprise software at Seed, Series A and Series B. Prior to joining SignalFire, Oana was at Scale Venture Partners where she invested in applied ML and developer tooling. Oana sourced Scale’s investments in Observe.ai, Flatfile, and Proscia. She was part of the deal teams for Honeycomb and AllyO (acquired by HireVue). She also supported existing portfolio companies such as Dialpad, Matillion, and BigID. Prior to Scale, Oana was an AI seed investor at SAP.io, SAP’s $35M seed fund, where she sourced the investments in Plum.io, Oto.ai, and Akorda.

In Today's Episode with Oana Olteanu We Discuss:

1.) From Tank Driving in Romania to VC's Rising Star:

• How Oana made her way from driving tanks in Romania to becoming a VC?
• How did leaving Romania for Germany and then moving to the West Coast impact her mindset?
• What does Oana know now that she wishes she had known when she entered VC?

2.) How to Assess a VC: The Founders Guide:

• Pre-investment, how can founders know whether a VC can add value? What are the signs?
• What three core questions will reveal how much value a VC can add?
• Post-investment, what can founders do to extract the most value from their VCs?
• What should the founders ask their investors for help with? What should they do themselves?

3.) The VC <> Founder Relationship:

• Oana has the highest founder NPS of any VC I have ever had on 20VC, what does Oana believe makes her founders rate her contribution so highly? What works? What does not?
• How does Oana give sometimes very hard feedback to founders but retain that relationship of trust and safety at the same time? What mistakes do other VCs make in giving feedback?
• What does Oana believe are the single biggest misalignment between VCs and founders?

4.) VCs Behaving Badly: 101

• What are the single biggest ways Oana sees VCs behaving badly?
• How does Oana think founders expectations of the product of venture should change?
• Does Oana believe boards are valuable? What can be done to improve them?

Items Mentioned in Today's Episode:

Oana's Favourite Book: The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living: Featuring new translations of Seneca, Epictetus, and Marcus Aurelius

Oliver Jay (OJ) is one of the most successful sales leaders of the last decade. Most recently, OJ spent 6 years as CRO @ Asana and grew the team from 20 to over 450, becoming a master in sales onboarding in the process. Before Asana, OJ spent 4 years at Dropbox, where OJ was Head of APAC & LATAM.

Jordan Van Horn is a Revenue Leader @ Monte Carlo. Prior to this role, Jordan spent 4 years at Segment as VP of Sales, leading a sales team of 50+ Account Executives. Before Segment, Jordan was at Dropbox for 4 years leading enterprise sales for Dropbox Business.

Dannie Herzberg is a Partner @ Sequoia Capital and before Sequoia, Dannie spent 4 years at Slack as their Head of Enterprise Sales, growing the business from $100M – $1B in revenue. Before Slack, Dannie spent over 5 years at Hubspot building sales teams.

Zhenya Loginov is the CRO @ Miro. At Miro, Zhenya runs the go-to-market team of 700+ people across. Prior to Miro, Zhenya was the COO @ Segment where he built and ran the global go-to-market team of 200+ people. Pre-Segment, Zhenya led a 100-person team at Dropbox across different functional areas.

Lauren Schwartz is VP of Enterprise Sales at Fivetran, where she has scaled the team to nearly 100, while more than tripling enterprise revenues. Previously, Lauren spent close to 4 years at Segment where she started as the first female AE and ultimately built and led sales teams in enterprise and growth.

Kyle Parrish is VP Sales @ Figma, where he built the sales engine from scratch to today, with over 100 in sales. Before Figma, Kyle spent over 5 years at Dropbox in numerous different roles including Head of Sales, and Global Partnerships lead, responsible for growing Dropbox’s partner ecosystem.

In Todays Episode on Sales Onboarding We Discuss:

1.) How should the onboarding process for all new sales reps be structured?

2.) How should the onboarding process for a new sales leader be structured?

3.) What specific things can leaders do to set both reps and leaders best up for success?

4.) What are the single biggest red flags in the first 30 days that a rep is not going to work out?

5.) What tools and software can be used to improve this process of ramping new reps?

Cathie Wood is the CEO & CIO @ ARK Invest, focusing solely on disruptive innovation, primarily in the public equity markets. ARK has become renowned for opening up its research and becoming a ‘sharing economy’ company in the asset management space. Prior to ARK, Cathie spent twelve years at AllianceBernstein as CIO of Global Thematic Strategies where she managed over $5 billion. Cathie joined Alliance Capital from Tupelo Capital Management, a hedge fund she co-founded, which managed $800 million in global thematic strategies. Prior to Tupelo Capital, she worked for 18 years with Jennison Associates LLC as Chief Economist, Portfolio Manager and Director. 

In Today's Episode with Cathie Wood We Discuss:

1.) Entry into Hedge Funds at 20:

• How did Cathie get her first role in the world of finance at the tender age of 20?
• What is Cathie running from? What is Cathie running towards?
• What are some of Cathie's biggest lessons from seeing the dot com bust at Tupelo?
• What does Cathie know now that she wishes she had known when she started investing?

2.) Why Benchmarks and Passive Investing are Bad:

• Why does Cathie believe that benchmarks and indexes have become dangerous for consumers?
• Why does Cathie not believe what everyone else does regarding inflation?
• How much of the performance of large-cap tech stocks is tied to the growth of passive investing?
• Why does Cathie think the Fed is making a huge mistake?

3.) Time to Pick Companies:

• Why does Cathie believe that Facebook is emerging as an attractive value stock?
• How does Cathie believe Elon Musk and Jack Dorsey could build the largest universal wallet?
• If Cathie were to put all her money into one of their companies, what would it be?
• Why does Cathie believe Zoom is one of the most misunderstood companies?

4.) Why Venture: Why Now:

• Why did Cathie decide to do a venture fund with ARK now?
• Why did Cathie decide to do a no-carry structure with a higher management fee? How does that align incentives with investors?
• In venture, the asset chooses the capital, how does Cathie analyze why the best founders in the world will pick and work with ARK over other amazing VCs?
• What is the single biggest risk you are underwriting when investing in ARK's venture fund?

Items Mentioned in Today's Episode:

Cathie's Favourite Book: The Emperor of All Maladies: A Biography of Cancer

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. Before joining General Atlantic in 2012, Martín was a Managing Director at Advent International. Prior to that, he was Co-Founder and CFO of Submarino.com, a leading Brazilian online retailer that went public and was sold to Lojas Americanas in 2006. Martin started his career as a management consultant at The Boston Consulting Group. Thanks to Seba Kanovich @ dlocal for the introduction today.

In Today's Episode with Martín Escobari:

1.) From Bolivia to Harvard to Leading General Atlantic:

• How did Martin make his way into the world of venture from a small town in Bolivia?
• How did being an operator going through a bust impact how Martin invests and works with founders?
• How does Martin advise young members on his team about surviving through a bust?

2.) Market Matters: Founders, Product or Market:

• Why does Martin believe the single most important element when investing is the market you are entering?
• How does Martin assess both market size and market growth?
• What does Martin believe makes a "beautiful business model"? What is the difference between good vs great? Why have we seen a generation of bad business models?
• How did Martin's analysis of Nubank's market lead him to turn them down? How did Martin change his approach to investing on the back of turning down Nubank?

3.) The Venture Landscape:

• What made Martin believe there was a downturn last year? What three signs always suggest we are in a bubble?
• As a result, how did General Atlantic retain their discipline when others did not? Where did they lose their discipline and invest at the top of the market?
• How does Martin analyse the performance of the crossover funds in the last 24 months? Who did well? Who did not? Do they remain in the market?
• Is Martin concerned by the exodus of capital out of South America with the bust?

4.) Martin Escobari: The Investor and Board Member:

• How has Martin's style of investing changed over the last decade?
• How does Martin reflect on his own price sensitivity? Does Martin engage in outcome scenario planning?
• What has been Martin's biggest hit? How did it change his mindset?
• How would Martin analyze his own style of board membership? How does Martin advise young board members gaining their first boards?

Hugo Barra is the OG of consumer hardware of the last decade. In Hugo's current position, he is the CEO @ Detect, building tools that empower people to understand their health and make informed, timely decisions. Before Detect, Hugo spent an incredible 4 years as VP of VR @ Meta with Oculus. Prior to Oculus, Hugo was in China as VP of Global @ Xiaomi, the 3rd largest phone maker in the world. Finally before Xiaomi, Hugo was a product leader @ Google for over 5 years including as VP of Android Product Management.

In Today's Episode with Hugo Barra We Discuss:

1.) Entry into Product:

• How did Hugo make his way from Brazil to Silicon Valley and Beijing Product OG?
• What is one takeaway from Google, Meta, and Xiaomi that influenced the way Hugo approaches product today?
• What is 996 Chinese work culture? How does the experience of working and leading teams in China impact his approach to team building today?

2.) The Secret to Success in Hardware:

• Why is hardware so much harder than software? What are the main differences?
• What are the biggest challenges faced when building V1 and V2 in hardware? How much do you rely on data vs gut and intuition?
• What are some of Hugo's biggest consumer product hardware failures? What did he learn from them?

3.) Feature King vs Budget King:

• Previously Hugo has said, "in the beginning, there is only two types of consumers." What does he mean by this? How does that impact his approach to product building?
• Can a budget king product leader also be an amazing feature king leader? What is the difference in the two? Why is it harder to be a budget king product leader?
• What happens if you have both budget king and feature king in one product? What happens then?

4.) Product Management 101:

• How does Hugo define product management today? What does it really mean to Hugo?
• Gustav @ Spotify has said before, "details are not details, they are the product." How does Hugo think about this statement in terms of great product management today?
• When do product orgs start to break down? What are the catalysts? What can be done to stop this?

5.) Brand Marketing vs Product Marketing:

• What is the difference between product and brand marketing?
• Why does Hugo believe you should always start every product build with the press release? What is the difference between good and great in a press release? What do the best have?
• What are the single biggest mistakes founders and product leaders make in storytelling today?

6.) Masterclass in Hiring:

• Why does Hugo do 3-and-a-half-hour interviews when hiring new candidates?
• What are the benefits of their being so long? What does he want to achieve?
• What core questions does he ask every time? What differentiates good from great?
• How does he get people to really open up and show true vulnerability?

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. Brian also raised venture funding before going public from some of the best including Fred Wilson @ USV, Micky Malka @ Ribbit, Marc Andreesen @ a16z and Garry and Alexis at Initialized. Prior to founding Coinbase, Brian was a Product Manager @ Airbnb.

In Today's Episode with Brian Armstrong We Discuss:

1.) Founding Coinbase:

• How did Brian make his way from PM @ Airbnb to founding Coinbase?
• What is Brian running from in his past? What is he running toward in his future?
• What does Brian know now that he wishes he had known at the start of Coinbase?

2.) Brian Armstrong: The Leader:

• What does "high performance" mean to Brian in leadership?
• How does Brian think about stepping off the treadmill for a second and appreciating what has been achieved? How does one celebrate as a team without creating laziness or arrogance?
• How has Brian most changed as a leader over the last 10 years?
• On reflection, what does Brian believe are his biggest weaknesses today?

3.) Crucible Moments in the Coinbase Journey:

• What does Brian mean when he says, "you need to be able to differentiate between a real emergency and a fame emergency?" What is the difference?
• When Brian made the speech to the Coinbase team on political views in the company, was that a real or fake emergency? What happened? What would he have done differently?
• Is the failed NFT launch, a real or fake emergency? What big mistakes were made? What are Coinbase doing to correct and improve them?
• "Bankrupt Coinbase" campaign on social earlier this year, real or fake emergency? What has been Brian's biggest lessons on how to deal with fake news?

4.) Crypto and The Ultimate Mission for Coinbase:

• What is different about this crypto winter from all other crypto winters?
• Why did Brian ban discussion on the market cap from employees within Coinbase?
• How does Brian maintain morale internally when everyone sees the stock at all-time lows?
• How does the Coinbase mission extend far beyond financial freedom for the world? What does Brian want Coinbase to be in 10 years?

Michael Mauboussin is Head of Consilient Research at Counterpoint Global. Previously, he was Director of Research at BlueMountain Capital, Head of Global Financial Strategies at Credit Suisse, and Chief Investment Strategist at Legg Mason Capital Management. He is also the author of three incredible books, including More Than You Know: Finding Financial Wisdom in Unconventional Places, named in The 100 Best Business Books of All Time by 800-CEO-Read. Michael has taught at Columbia Business School since 1993 and received the Dean's Award for Teaching Excellence in 2009 and 2016.

In Today's Episode with Michael Mauboussin We Discuss:

1.) Entry into Venture and Finance:

• What does Michael actually do as "Head of Consilient Research"?
• What does Michael know now that he wishes he had known when he entered finance?
• How did Michael and Bill Gurley meet in business school? What does Michael believe makes Bill such a special investor today?

2.) Booms and Busts: How This Compares?

• How does the current macro downturn compare to prior crashes Michael has worked through?
• What is the same? What is different? How do political and health events impact the macro?
• Why was 1987 the end of the world at the time? How did the recovery take place?
• How does Michael analyze the duration of bull markets vs the duration of recovery time?
• What advice does Michael give to young people today questioning if they are good investors?

3.) The Investment Decision-Making Process:

• How does Michael advise on the structuring of your decision-making process?
• What makes a good process vs a bad process?
• What can be done to remove politics from the decision-making process?
• What can be done to ensure all people, regardless of hierarchy feel safe in the process and feel they can share their thoughts without repercussions?
• What are the single biggest mistakes Michael sees people make in their decision-making process?
• How do you know when is the right time to change your process?

4.) Everything is a DCF:

• What does Michael mean when he says that "everything is a DCF"?
• How does Michael advise and apply this thinking to early-stage venture investors?
• How does Michael think through highly diversified portfolios vs super concentrated portfolios in venture?

Items Mentioned in Today's Episode:

Michael's Favourite Book: Consilience: The Unity of Knowledge by E.O Wilson

Raf Illishayev is the Co-Founder and CEO @ GoPuff, one of the market leaders delivering daily essentials in minutes. GoPuff’s latest funding round priced the company at a reported $8.9Bn in March 2021 and to date, Rafael has raised over $2.4Bn for the company from the likes of Accel, Softbank, Fidelity, Baillie Gifford, D1 Capital and more. Rafael has scaled the company to over 1/3 of the US with over 12,000 employees nationwide.

In Today’s Episode with GoPuff's Rafael Ilishayev You Will Learn:

1.) From Student to Global CEO:

• How Raf came up with the idea for GoPuff and started the company as a student with no funding?
• What were the early signs of product-market fit that Raf observed in the early days?
• In hindsight, does Raf wish they had raised external funding sooner than they did? What would raising external funding sooner have changed about the way they run the business?

2.) The Rise and Fall of Quick Commerce:

• What are the core drivers that have led to capital drying up for players in the quick commerce space?
• With the changing environment, is it a race to profitability for all providers in the space?
• Is this the perfect time for GoPuff to acquire? What are the characteristics of businesses in the space that GoPuff would vs would not like to acquire?
• How does Raf see the quick commerce space looking in 5 years time?

3.) Getting to Profitability: The Levers That Matter:

• Customer Service: Why does Raf believe that all players pulling back on investing in customer service are making a massive mistake? What can be done instead?
• Delivery Time: Why does Raf believe the 10-minute delivery model is fundamentally unprofitable? How do GoPuff approach it as a result?
• Inventory: With a changing macro-environment, why does Raf believe it is prudent to focus more attention on alcohol and convenience goods? What do prior recessions show us about consumer spending patterns changing?
• Metrics: What are the single most important metrics which dictate the speed of getting to profitability? Why is the amount of orders a driver can deliver per hour the most important metric?

4.) Business Expansion Opportunities:

• How does Raf analyze the opportunity for GoPuff in Europe?
• Why does Raf believe they should have pulled out of Spain much sooner? Why are they so focused on the UK now?
• Why does Raf believe it is the right decision to stop investing in GoPuff pharmacy?
• Why is Raf so bullish on GoPuff kitchens? How does the unit economics of the kitchens compare to the core business for GoPuff? What are the positive effects of kitchens on GoPuff core product?
• What was the most recent disagreement the board has had when it comes to determining what to prioritize vs what not to?

Mentioned in Today's GoPuff Episode:

Raf's Mentor and Advisor: Emil Michael, Former Chief Business Officer @ Uber

Brian Singerman is a Partner @ Founders Fund, one of the best-performing funds of the last two decades. Among their portfolio, they have the likes of Airbnb, Facebook, Stripe, Anduril, and many more generational-defining companies. As for Brian, he has led investments in the likes of Affirm, Oscar Health, Wish, Asana, Oculus, and Postmates to name a few. Brian also sits on the board or is an observer to The Long Term Stock Exchange, Solugen, Cloud9, Modern Health, and of course, Anduril. Prior to Founders Fund, Brian spent a very successful 4 years as an engineer and executive at Google.

In Today's Episode with Brian Singerman We Discuss:

1.) From Google to Befriending Sean Parker to Founders Fund:

• How Brian's friendship with Sean Parker led to his joining Founders Fund over 15 years ago?
• What does Brian believe makes Founders Fund such a unique fund?
• What does Brian know now that he wishes he had known when he started in venture?

2.) The Landscape Today: Where Are We Now?

• Why does Brian believe there is a huge price mismatch between private vs public companies?
• How does this impact the pace with which Founders Fund invest? Why does Brian not feel any pressure to invest in this environment?
• What are the 10 hypergrowth companies that Brian is looking to invest in today?
• What advice does Brian give to young investors today who are concerned at their first market correction and questioning if they are actually any good at this?

3.) Brian Singerman: The Investor:

• How does Brian reflect on his own investing style? What is he world-class at? What is he bad at?
• Why does Brian think boards are a waste of time? What is better than a board?
• Why does Brian not ever think about reserves? How does Brian answer LPs concerns when they cite them on the topic of cross-fund investing?
• What does Brian believe is the secret to venture capital? What elements make those at Founders Fund thrive? What characteristics make those that do not work out, fail?

4.) Founders Fund: The Firm:

• How does Founders Fund structure and optimize its decision-making process today?
• How does Founders Fund approach the hiring process for all new team members? What one question do they need to be able to clearly answer with all team members joining?
• How do Founders Fund approach the reference checking process for all new hires? What questions do they find most revealing of the true talent of the candidate?
• What are the single biggest hiring mistakes Brian has made? What did he learn from them?

Items Mentioned in Today's Episode:

Brian's Most Recent Investment: Anduril

Chris Sacca is the Founder and Chairman @ Lowercase Capital, one of the best performing funds in the history of venture capital with a portfolio including Uber, Stripe, Twitter, Instagram, Twilio, Docker and many more.

• From interviewing some of the world's richest married couples, how did gaining wealth change their relationship and marriage?
• What does Chris do to actively ensure his children remain hungry and know the value of money?

Chamath Palihapitiya is Founder & CEO @ Social Capital. Social’s portfolio includes the likes of Slack, Yammer, Front, Intercom and Carta to name a few.

• What does Chamath mean when he says we need to think through the mindset of "infinite games" not finite games? How does this change how you think about money?
• How does Chamath think about his relationship to risk today as a result?

Brad Gerstner is the Founder and CEO of Altimeter. Brad’s notable deals that he has helped lead include Snowflake, Mongo, Bytedance, Gusto, Unity, Okta, dbt, Modern Treasury, EPIC Games, Hotel Tonight and Zillow.

• What is the most important thing parents can do to ensure that despite wealth, their children remain grounded and ambitious?
• Why does Brad, despite being a billionaire, still live in a modest house and not spend on the excesses of life? How does Brad embrace essentialism with wealth?

Cyan Banister is one of the most successful and renowned early-stage investors in the last decade. Her portfolio includes the likes of SpaceX, Uber, Affirm, Opendoor Postmates, Niantic and Thumbtack to name a few.

• Why did Cyan used to hate money? Why was she "anti-capitalist"?
• How does Cyan approach risk management today? Why does she invest every dollar she makes back into the ecosystem?

George Zachary is a General Partner @ CRV, one of the nation's oldest and most successful early-stage venture capital firms with a portfolio including the likes of Airtable, DoorDash, Dropbox, Niantic and many more.

• What did George learn about how the way people view you changes with your increasing wealth?
• Why does George believe rich people like to hang out with rich people?

Biz Stone is best known as the Co-Founder of Twitter and Medium. Biz is also an investor in the likes of Slack, Square, Intercom, Beyond Meat and Blue Bottle Coffee.

• What does Biz mean when he says, "wealth only serves to amplify the person you are?"

Vaibhav Sahgal is VP of Consumer Product @ Reddit where he has been for close to 5 years. Prior to his leading consumer product, Vaibhav spent 3 years as Head of Growth at Reddit. Before Reddit, Vaibhav spent an incredible 8 years at Zynga across different roles including Director of Product and GM for "Words with Friends".

In Today's Episode with Vaibhav Sahgal We Discuss:

1.) Entry into Product + Growth:

• How did Vaibhav come to lead some of the best growth orgs in the world at both Reddit and Zynga?
• What are 1-2 of Vaibhav's biggest takeaways from working with Mark Pincus @ Zynga?
• What is the most painful growth lesson that Vaibhav learned that he is also pleased to have learned?

2.) WTF Really is "Growth":

• How does Vaibhav define growth today? What is it not?
• How does Vaibhav fundamentally differentiate between value connection and value creation?
• Is growth an art or a science? What tactics have died a death? What remains stronger than ever?

3.) Hiring Your Growth Team:

• How does Vaibhav advise founders on when is the right time to hire their first growth professionals?
• Where should they sit within the org? In product? In marketing? Standalone growth team?
• What are the biggest mistakes Vaibhav sees founders make when hiring their first growth hires?

4.) The Interview Process:

• How does Vaibhav structure the interview process for all new growth hires? What are the steps?
• What are the must-ask questions when hiring for growth? What are good answers?
• How can founders use case studies and data to determine the quality of a growth candidate?

5.) The Onboarding and Integration:

• What is the optimal onboarding process for all new growth hires?
• What are signs in the first 3 days that a growth hire will vs will not work out?
• What can leaders do to ensure growth hires are integrated with the rest of the teams?
• What are the biggest mistakes founders make when onboarding growth hires?

Items Mentioned in Today's Episode:

Vaibhav's Favourite Book: Andrew Chen: The Cold Start Problem

Emil Michael is the Former Chief Business Officer at Uber and is commonly referred to as Travis Kalanick's right-hand man. At Uber, Emil was instrumental in raising nearly $15BN from some of the largest investors in the world, making Uber the most valuable private tech company ever. Emil was also core to Uber's China strategy and led deals with Didi and Baidu. Before Uber, Emil spent 9 years at TellMe Networks where he was central to Microsoft raising their acquisition price from $300M to $800M. Emil is also an advisor to some of the greats including Raf @ GoPuff, Zach @ Codeacademy, Jared @ Fundera and many more.

In Todays Episode with Emil Michael:

1.) From Politics to Travis's right-hand man at Uber:

• How did Emil make his way into the world of startups with TellMe networks?
• Harvard, Stanford, Goldman, Politics, which career shaped Emil the most?
• When Emil looks at his cohort of Ali and Hadi Partovi, Alfred Lin, and many others, what did they have that Emil believes is core to their success today?

2.) Negotiations 101: A Masterclass:

• What is Emil's framework for dealmaking? How has it changed over time?
• What are the single most important elements to remember when making deals?
• What are the biggest mistakes people make when negotiating?
• What is the right way to use leverage in negotiations?
• How can one handle an opponent that is emotional or irrational when negotiating?
• How did Emil make Steve Ballmer @ Microsoft increase his offer for TellMe from $300M to $800M?
• What is the single deal that Emil made that he regrets the most?

3.) Uber: The Journey to the Most Valuable Private Company:

• Why were Emil and Travis removed from Uber? Does Emil think it was fair?
• Is it true that Travis lost the support of the team? How did his removal take place?
• How did the Uber China deal go down with Didi? What got DiDi over the line on the deal?
• How did Emil raise $3BN from Saudi in just 60 days with Travis needing to attend only one meeting?

4.) Uber: The Review:

• How does Emil assess the management and performance of Uber CEO, Dara Khosrowshahi?
• If Travis and Emil were still in charge, what would Emil have done differently?
• Why does Emil think Dara and Uber have made a $30BN mistake in food delivery?
• Why does Emil think Postmates, Careem, and others have been the worst acquisitions in tech?

5.) The Venture Landscape:

• Emil entered the world of VC with Coatue, why did he decide that VC was not for him?
• How does Emil analyze the VC landscape today? Who are risers? Who are fallers?
• What are the single biggest points of misalignment between founder and VC?
• What are the core improvements that Emil would like to see made to the VC world?

Items Mentioned in Today's Episode:

Emil's Favourite Book: Sun Tzu: The Art of War

Kyle Harrison is a General Partner @ Contrary and one of my favorite writers on the venture space with his blog, Investing 101 2.0. Before joining Contrary, Kyle worked in the ranks of some of the biggest and best names in venture, starting with a spell at TCV before moving to Coatue and making his final stop at Index. Across firms, Kyle has led or participated in investments including Ramp, Pave, Anduril, Gitlab, Databricks and Snowflake to name a few.

In Today's Episode with Kyle Harrison:

1.) From Film Lover to Technology Investor:

• How Kyle went from creating a professional services marketplace around film to joining the ranks of TCV and investing in breakout technology companies?
• What was Kyle's biggest takeaway from TCV? How did it impact his mindset?
• What was Kyle's biggest lesson from working with the Laffont's at Coatue? How did it change the way he thinks about price and market sizing?
• Why was Index such a transformational school of venture for Kyle? How did that experience change how he thinks about what it takes to be a great investor?

2.) The Death of So So Venture Firms:

• Why does Kyle believe many of the "so so" venture firms will die?
• What does Kyle believe makes a venture firm "so so"? Who is vulnerable then?
• How does Kyle think the lifespan and "death" of venture firms will change in the next decade?

3.) The Rise of "The Blackstone of Venture Firms":

• How does Kyle define "the Blackstone of VCs"? Who are they?
• With increasing fund sizes will we see VC returns denigrate to PE returns?
• How is the world of family offices changing the venture environment? Will we see more or less money flood into venture over the coming years?
• Of the incumbents, who has done "The Blackstone" model well? Why? Who has failed? Why?

4.) The Rise of Community in Venture:

• What does "community" really mean to Kyle? Why does he believe it will play such a prominent role in the way the best invest in the future?
• How have existing players failed to build, sustain and productize communities?
• What are the best opportunities for new entrants to create and utilise communities to invest?

Items Mentioned in Today's Episode:

Kyle's Favourite Book: Reinventing Knowledge: From Alexandria to the Internet

Lauren Schwartz is Vice President of Enterprise Sales at Fivetran, the leading platform for modern data movement. She has helped scale Fivetran's enterprise business from its infancy to a team of nearly 100, while more than tripling enterprise revenues. Previously, Lauren spent close to 4 years at Segment where she started as the first female AE and ultimately built and led sales teams in enterprise and growth. Lauren earned an MBA from Stanford Graduate School of Business after 6 years at Google where her enterprise sales career began.  

In Today's Episode with Lauren Schwartz:

1.) How Being Rejected as an Eighth Grader Can Lead to World Class Sales Leader:

• How Lauren made her way into the world of enterprise sales with Google?
• Why, for a while, Lauren wanted to get away from the label of a salesperson? Why "salesperson" does not do the job of sales justice?
• Why does Lauren believe that one of the core traits the best salespeople have is being able to cope with rejection? How has Lauren been rejected? How did she respond? What changed their mind?

2.) The Sales Playbook: What, Who, When:

• How does Lauren define the term "sales playbook"? What are the nuances?
• Does Lauren believe the founder should always be the first sales rep? What are the core signs that a founder is now ready to bring in their first sales hires?
• What are the 3 biggest mistakes founders make when they hire their first sales reps?
• What are the core traits that the best early sales reps have?

3.) The Hiring Process: Building the Best Sales Team:

• How does Lauren structure the hiring process?
• What are the most unconventional but useful questions Lauren uses to determine the depth and quality of potential sales hires?
• What are the glaring red flags that Lauren looks for in this interview process?
• How does Lauren use case studies and deal reviews in the interview process to determine the quality of a candidate?

4.) Scaling the Machine: The Onboarding Process:

• What are the single biggest mistakes founders make when onboarding sales reps?
• How should sales team onboarding be structured?
• What materials should the founder have in place for the sales team to learn from on Day 1?
• How can sales leaders ensure new sales team members engage across functions?

Drew Houston is the Co-Founder and CEO @ Dropbox, for over 700 million users and +600,000 teams, Dropbox is the choice for storing and sharing their most important files. Prior to their IPO in 2018, Drew raised funding from some of the best including Sequoia, Index, Greylock, and IVP to name a few. Drew also currently sits on the board of Meta and is a seasoned angel with a portfolio including Gusto, Scale AI, Pilot and Superhuman to name a few. Prior to Dropbox, Drew founded Accolade, a bootstrapped online SAT prep company he started while in college.

In Today's Episode with Drew Houston We Discuss:

1.) Entry into Startups and Y Combinator:

• How did Drew make his way into the world of startups with an SAT prep planning startup?
• How did Drew convince Paul Graham to accept him and Dropbox into Y Combinator?
• If we are all a function of our pasts, what is Drew running towards and what is he running away from?

2.) Drew Houston: The Leader and CEO:

• How does Drew define "high performance" today?
• How would Drew describe his style of management? How has it changed over time?
• How did taking an enneagram test change how Drew leads? What did he learn?
• What have been Drew's biggest hiring mistakes? What mistakes does he see others make?
• What have been Drew's biggest lessons in how to let people go the right way?

3.) Crucible Moments: Getting Sequoia, Acquisitions and Steve Jobs:

• How did Drew convince the Sequoia team to invest in Dropbox? How did it all start in a rug shop thanks to Pejman Nozad @ Pear?
• Has Drew had opportunities to sell the company? Why did he not take them? How does he advise founders on the decision to sell or not?
• How did Drew come to meet Steve Jobs? How did the meeting go?

4.) Drew Houston: AMA:

• Is Dropbox a B2B company or a B2C company?
• What is the hardest element of Drew's role with Dropbox?
• What has Drew recently changed his mind on?
• When press cycles were against him, how did Drew get through those tough times?
• What is Drew's biggest takeaway from joining the Meta board?

Items Mentioned In Today's Episode:

Drew's Fave Book: High Output Management by And

Tristan Handy is the Founder and CEO @ dbt, a data transformation tool that enables data analysts and engineers to transform, test and document data in the cloud data warehouse. To date, Tristan has raised over $400M from the likes of Sequoia, Altimeter, Coatue, ICONIQ and GV with the latest funding round valuing the company at $4.2BN. Prior to founding dbt, Tristan was the VP Marketing @ RJ Metrics and got his break in the world of startups through former 20VC guest, Anthony Casalena with a Director of Operations role at Squarespace.

In Today's Episode with Tristan Handy:

1.) Entry into Startups:

• How did Tristan make his way into the world of startups with his first role at Squarespace?
• How did Tristan's time with Squarespace impact how he builds dbt today?
• What does Tristan know now that he wishes he had known when he founded dbt?

2.) Our Jobs Are Not That Hard:

• Why does Tristan believe that our jobs are not that hard?
• If going down this line, how does Tristan hire? What does he look for? How does he test for it?
• When does experience matter? When does it not matter?

3.) dbt: The Company

• Why does Tristan believe that remote work does not work?
• What financial packages have dbt put in place to allow their employees this physical interaction?
• What does Tristan believe is the hardest element of building a hybrid company? When does everything start to break?
• What are the biggest lessons Tristan and dbt have taken from Gitlab?

4.) Tristan: The Leader

• How does Tristan conduct and execute on the best performance reviews?
• How does Tristan create an environment of safety where people feel they can be honest and transparent?
• What are the elements that you cannot be transparent on? Where does transparency break down?

5.) Trading Freedom for Scale:

• dbt could have been a small and super profitable company, why did Tristan decide to trade off the freedom and raise big from VCs?
• How did Tristan raise over $414M without ever talking about an efficiency metric?
• Is Tristan concerned about living into the $4.2BN valuation in what is a very different time?
• With the benefit of hindsight, is Tristan pleased he went big and raised venture?

Gustav Söderström is Spotify’s Chief Research & Development Officer. He has the CPO & CTO responsibility, overseeing the product, design, data, and engineering teams at Spotify and is responsible for Spotify’s product strategy. Gustav is also an entrepreneur and investor who has founded and sold startups that he co-founded to Meta’s Oculus in 2014 and then also his first startup which he co-founded and led as CEO, up until their acquisition by Yahoo! Gustav is also the host of the podcast mini-series  -- Spotify: A product story -- which offers a glimpse into the decisions that have guided Spotify’s product evolution.

In Today's Episode with Gustav Söderström

1.) From Selling Companies to Yahoo and Meta to Leading Spotify's Product:

• How did Gustav first make his way into the world of tech and startups?
• What was it that made Gustav so compelled to join Daniel Ek and build Spotify?
• What does Gustav know now that he wishes he had known when he started?

2.) "Never Fight a Macro Wind":

• What does Gustav mean when he says "never fight a macro wind"?
• What models can product leaders construct to measure the size, importance and timing of a macro wind?
• What can product leaders do to change the macro wind and have it blowing in their back and not their face?
• When did Gustav experience this? What did he change to have the wind blow in his back? How did this alter his mindset and mentality?

3.) "Do Something Completely Different to the Competition":

• Why does Gustav believe startups should do the complete opposite to the competition? Does this change if your competition is other startups vs incumbents?
• What is the story of how Spotify did the complete opposite to Youtube? Why did it work?
• On the flip side, when did Spotify do the complete opposite and it did not work out?

4.) Mastering the Learning Process:

• How does Gustav approach the learning process for all new skills and disciplines?
• Why does Gustav believe that all technology leaders have to be the master of their domain? How did this lead to Gustav going back to University to study machine learning?
• What are the single biggest mistakes people make in the learning process?

5.) Gustav: The Product Leader:

• Why does Gustav believe that product is 100% science and not art?
• What does Gustav mean when he says, "talk is cheap and so we should do more of it"?
• How does Gustav structure internal debates? Who sets the agenda? Who is invited? What makes a good vs a bad internal debate?
• How does Gustav make everyone feel safe? What can leaders do to ensure an environment where everyone feels they can debate with the boss?

6.) Spotify: The Crucible Moments:

• What is Gustav's favourite near-death experience in the Spotify journey?
• Why did Spotify decide to make the move into podcasting and video? How does that additional complexity change the product paradigm of an audio-only platform?
• How do the single most impactful platforms in the world approach market expansion and when to add new products?
• What are the best companies in the world not merely technology innovations but also business model innovations?

Items Mentioned in Today's Episode:

EXCLUSIVE NordVPN Deal ➼ https://nordvpn.com/20vc Try it risk-free now with a 30-day money-back guarantee!

Brad Gerstner is the Founder and CEO of Altimeter, a life-cycle technology investment firm that manages public and private portfolios. Brad has personally participated in more than 100 IPOs as a sponsor, anchor, and investor. Brad’s notable deals include Snowflake, Mongo, Bytedance, Gusto, Unity, Okta, dbt, Modern Treasury, EPIC Games, Hotel Tonight, and Zillow. Prior to founding Altimeter, Brad was a 3-time co-founder where he sold all three businesses (to IAC, Google, and Marchex), a founding principal at General Catalyst; a securities lawyer, a former Deputy Secretary of State of Indiana, and a pilot.

In Today's Episode with Brad Gerstner We Discuss:

1.) From Humble Beginnings in Indiana to 100 IPOs:

• When did Brad realize his original love of finance and entrepreneurship?
• What one single question does Brad ask all potential new recruits to determine if they have hustle?
• What does Brad know now that he wishes he had known at the beginning of his career?

2.) The Power Law and Supercycles:

• What is a power law? Why is it the single most important thing in investing?
• How do the best investors in the world build a framework around supercycles?
• How does Brad approach market sizing? How does Brad think about market creation when aligning that to his thesis of investing in power laws?
• How does Brad determine if a large opportunity is a "super-cyle" or a short, time-stamped fad that is unsustainable? How does Brad assess the importance of market timing?

3.) Building Anti-Fragile Portfolios:

• Portfolio Construction: Why does Brad disagree that the answer to risk mitigation is portfolio diversification? How many companies is enough companies for a diverse portfolio?
• Price Sensitivity: How does Brad reflect on his own relationship to price? How does this process and mindset change on re-investments? What is needed for Brad to re-invest?
• Time to Exit: How does Brad analyze when is the right time to exit a position? What are the single biggest mistakes people make when it comes to timing their exit?

4.) The Venture Landscape: Today, What is Happening?

• Why does Brad believe what has happened over the last 24 months is a great disservice to founders?
• What are the biggest examples of a complete lack of investor discipline?
• Why does Brad believe that for all positions valued over $500M, we should apply a 20% discount?
• Is today's pricing actually just the new normal? How has the public market pricing impacted the deployment of growth stage checks? How will this play out in the next 12 months?
• Why does Brad believe there is "not blood on the streets yet"? How does the speed of interest rate change impact our ecosystem so dramatically?

Items Mentioned in Today's Episode:

Brad's Favourite Book: The Snowball: Warren Buffet and the Business of Life

Kevin Weil is President of Product and Business @ Planet and Operator in Residence @ Scribble Ventures. In the past, Kevin has been Head of Product at Twitter, Instagram, and Novi (the digital currency effort within Facebook). During his seven years at Twitter, he helped the company scale from 40 to 4000 people and from $0 to $2B in revenue. He then moved to Instagram in 2016 to lead the product and data teams and led through an inflection point as Instagram grew from 400M to over 1B users, including launching Instagram Stories. Kevin then co-founded Diem (formerly known as Libra) and Novi and built both for three years before moving to Planet in 2021. If that was not enough, Kevin is also on the board of Strava, the Nature Conservancy, and the Black Product Managers Network.

In Today's Episode with Kevin Weil We Discuss:

1.) Lessons From Leading Product for Instagram and Twitter:

• What does Kevin believe makes Instagram so inherently good at product? How did leading product for Instagram change the way Kevin thinks and operates?
• What are 1-2 of Kevin's biggest lessons from working with Kevin Systrom, Instagram's Founder?
• What are the biggest takeaways for Kevin from leading product at Twitter?

2.) Launching Products, Customer Discovery and Product Sessions:

• What were Kevin's biggest learnings from launching Instagram stories? How did Kevin's conviction impact the product building and success of Instagram stories?
• How does Kevin advise founders on the best way to approach customer discovery? What are the best questions to ask to reveal the truth?
• How does Kevin approach product testing today? Why does Kevin not like softly softly testing new products?

3.) Kevin Weil: Leadership 101

• What are some of the biggest leadership mistakes that Kevin made in his time at Twitter?
• How does Kevin approach decision-making frameworks? How does one balance the speed vs the quality of the decision?
• What makes a great product strategy? Where do so many go wrong in their product strategy?
• How do the best leaders communicate with their team? How does this change over time?
• What is Kevin's preferred medium and style of communication with his teams?

4.) Kevin Weil: The Athlete, Father and Husband:

• Kevin is an ultra-marathon runner, what does his training routine look like?
• What 1-2 changes has Kevin made that have had the biggest impact on performance?
• How does Kevin manage, investing, advising, training and being a father and husband?

Geoff Lewis is a Founder and Managing Partner of Bedrock, one of the breakout and new venture firms of the last decade, famously in search of narrative violations. He serves or has served on the Board of Directors for companies including Lyft (NASDAQ: LYFT), Nubank (NYSE: NU), Epirus, and Vercel. Additionally, he has led sizable early-stage venture capital investments in dozens of companies including Upstart (NASDAQ: UPST), Tilray (NASDAQ: TLRY), Leafly (NASDAQ: LFLY), Wish (NASDAQ: WISH), Workrise, and Rippling. Prior to founding Bedrock, Geoff served as a partner at Founders Fund for several years.

In Today's Episode with Geoff Lewis:

1.) Meeting Parker Conrad: A Generational Defining Entrepreneur:

• How did Geoff first come to meet Parker Conrad, over a decade prior to making the first Rippling investment?
• What was it about Parker that compelled Geoff so much in the early days?
• How did Geoff analyze the chip on Parker's shoulder from Zenefits? How does he believe it has driven him with Rippling?

2.) Searching for Narrative Violations in Rippling:

• Why does Geoff believe Parker himself is a "narrative violation"?
• What does Geoff believe is the foundational narrative violation in the way Parker is building Rippling?
• Rippling has a large portion of its team as former founders, how does Geoff believe this impacts the culture of Rippling?
• What does Geoff believe are the single biggest barriers to Rippling being the "App Store for Business"?
• On the upside case, if Rippling goes right, how big could this be?

3.) Rippling: The Financing:

• What has been Geoff's biggest lesson on price and price sensitivity that he has learned through Rippling?
• Why does Geoff never do uncapped notes? Why did Geoff break that rule with Rippling?
• What gave Geoff the conviction to write Bedrock's largest ever check in Rippling's Series D?
• What was the massive mistake that both Geoff and Bedrock made in not financing their Series C?

4.) Geoff Lewis: The Investor

• What single trait does Geoff believe all generational defining founders share? How does he test for it?
• Does Geoff believe he has a chip on his shoulder today? How has his relationship to the chip on his shoulder changed over time?
• To what extent does Geoff engage in outcome scenario planning when making investments?
• What upside scenario plan does Geoff need to be able to see for him to make an investment?
• Has Geoff ever lost money in an investment? What were his takeaways from this experience?

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. To date, Parker has raised over $697M for Rippling from some of the best including Sequoia, Founders Fund, Greenoaks, Bedrock, Kleiner Perkins and Initialized to name a few. Prior to founding Rippling, Parker was the Co-Founder and CEO @ Zenefits and if that was not enough, Parker is also a prominent angel having invested in Census, Pulley and then also AgentSync and TrueNorth, alongside 20VC Fund.

In Today's Episode with Parker Conrad:

1.) Entry in Startups and Zenefits:

• How did Parker make his way into the world of startups?
• How did Parker end up being kicked out of his own company, Zenefits? How did he respond?
• How did that experience of being kicked out of Zenefits inspire him to build Rippling?

2.) Parker Conrad: The Leader:

• How does Parker define "high performance"? How would Parker describe his leadership style today?
• Why does Parker fundamentally disagree that with speed comes a trade-off in quality? How does Parker ensure Rippling does all things fast and to the best of its ability?
• How would Parker break down his decision-making framework today? How does he decide what to prioritize vs not? How does he decide what to delegate vs not?
• What are Parker's biggest insecurities in leadership today? How have they changed over time? What does Parker do to combat and mitigate them?

3.) Rippling: The Compound Startup

• How does Parker define a compound startup?
• What types of business do this verticalized approach work for vs not work for?
• What does Parker believe are the 4 core benefits of this approach?
• What are the single biggest challenges of building a compound startup?

4.) Rippling: The Economics:

• How does this compound startup approach impact ability to cross-sell? How much net new ARR today comes from cross-sell?
• What have been some of Rippling's biggest lessons on what it takes to do cross-sell so effectively?
• How do the margin profiles differ across their different products? How have the margin profiles changed over time?
• Why does Parker not believe that most startup margins are accurate?
• How does the compound startup approach change the amount invested in R&D? How does that impact the fundraising requirements of the business?

5.) Rippling: The Partner Ecosystem:

• How does Rippling think about building out the best partner ecosystem? What will it take for that to work?
• Why do Rippling want to introduce services that compete with their own products? Why do they not only build their own?
• How do the margins differ when comparing revenue share on partner products vs Rippling products?
• What are the single biggest barriers to this partner ecosystem working?