The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. If you would like to see more of The Twenty Minute VC (20VC), head to for more information on the podcast, show notes, resources and more.
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Now displaying: October, 2022
Oct 31, 2022

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

Oct 28, 2022

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?"

Oct 26, 2022

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

Oct 24, 2022

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

Oct 21, 2022

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

Oct 19, 2022

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?

Oct 17, 2022

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

Oct 14, 2022

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?
Oct 12, 2022

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 ➼ Try it risk-free now with a 30-day money-back guarantee!

Oct 10, 2022

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

Oct 7, 2022

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?


Oct 5, 2022

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?

Oct 3, 2022

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?