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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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?

Sep 30, 2022

Tarek Mansour is the Founder and CEO @ Kalshi, the first regulated exchange where you can trade directly on the outcome of events. Tarek has raised funding from some of the best including Alfred Lin @ Sequoia, Ali Partovi @ Neo, Ron Conway, Charles Schwab and Henry Kravis. Before founding Kalshi, Tarek worked at the likes of Citadel, Palantir and Goldman Sachs, in various different roles.

In Today's Episode with Tarek Mansour We Discuss:

1.) Entry into Startups:

  • How did Tarek make his way from a nerdy kid in Lebanon to having his first startup funded by Sequoia and billionaires likes Charles Schwab and Henry Kravis?
  • How did his mother's continuous desire for excellence change Tarek's mindset?
  • What are the biggest lessons that Tarek took from his mother's strict parenting and how did he apply them to how he manages the team at Kalshi today?

2.) What it Takes to Succeed:

  • Why does Tarek believe that the world does not want your startup to exist?
  • In that case, what are the core traits that founders need to fight this headwind?
  • Does Tarek believe in work-life balance? What are some of the struggles of this?
  • Does Tarek believe you should work on your weaknesses or double down on your strengths?

3.) Building the Team:

  • Does Tarek believe that naivete is a strength or a weakness? At what point does it change between being a strength to being a weakness?
  • Does Tarek prefer to hire more senior experienced people or younger hustlers with more energy?
  • What have been the single biggest hiring mistakes that Tarek has made? How has it changed his approach to team building?
  • What is the one single trait that if Tarek sees, he will not hire?
  • How does Tarek make the interview process both fun but different and challenging?
  • Where do so many founders make mistakes in how they construct the hiring process?

4.) Tarek Mansour: AMA:

  • What have been the single biggest lessons from working with Ron Conway and Alfred Lin?
  • What are some of Tarek's biggest insecurities in leadership today?
  • What does Tarek know now that he wishes he had known at the beginning of his time with Kalshi?
  • What would Tarek most like to change about the world of startups?

Items Mentioned in Today's Show:

Tarek's Favourite Book: Never Split the Difference: Negotiating as If Your Life Depended on It 

Sep 28, 2022

Kipp Bodnar is the Chief Marketing Officer of HubSpot, where he sets HubSpot’s global inbound marketing strategy. Prior to his role as CMO, Kipp served as VP of Marketing at HubSpot, overseeing all demand generation activity worldwide and building out the EMEA and APAC marketing teams. Kipp serves as a marketing advisor for SimplyMeasured, InsightSquared and Guidebook. Kipp is the co-author of “The B2B Social Media Book: Become a Marketing Superstar by Generating Leads with Blogging, LinkedIn, Twitter, Facebook, Email, and More.”

In Today's Episode with Kipp Bodnar We Discuss:

1.) The Journey to CMO @ Hubspot:

  • How Kipp made his way into the world of marketing and came to be CMO @ Hubspot?
  • What does Kipp know now that he wishes all CMOs knew when they started?

2.) Choosing The Channel:

  • How does Kipp advise founders on which channel they should focus on? What is the framework which will tell them which channel is right for them?
  • How many different channels should they try? How focussed should they be? Should they have independent teams for each channel?
  • How do the best founders allocate resources to new channels? How do you know when one is not working and you need to stop? When do you just need to keep going and persisting?
  • What have been some of Kipp's biggest mistakes when entering new channels?

3.) Product Marketing, Brand Marketing and Founders Marketing:

  • How does Kipp advise founders who say that, "social and personal brand is just not for them"?
  • In what two ways does Kipp believe that all businesses are constrained?
  • Does Kipp agree that the state of product marketing has never been worse? What is truly great product marketing to Kipp?
  • How does Kipp distinguish between good and great brand marketing? How has what it takes to be great at brand marketing changed over time?

4.) The Best Marketing People:

  • What are signs of clear 10x performers in marketing?
  • What advice would Kipp give to someone aspiring to be a CMO? What mistakes do 95% make that they should change?
  • How do the best CMOs manage up and manage their team? Why does Kipp compare the role of the CMO to the general manager in NFL teams?
  • Why does Kipp believe the role of the CMO is a lonely one? What are the hardest elements?
  • What framework for learning does Kipp use to learn all new topics? What works? What does not?

Sep 26, 2022

Paul Davison is the Co-Founder and CEO @ Clubhouse, the startup that believes people are at the centre of every moment, providing a platform to talk with friends and meet new friends. To date, Paul has raised over $310M with Clubhouse from a16z, DST, Elad Gil, Naval Ravikant, and many more. Prior to co-founding Clubhouse, Paul was the Founder of Highlight, a location-based consumer social service backed by Benchmark. Before Highlight, Paul actually spent time at Benchmark as an EiR.

In Today's Episode with Paul Davison We Discuss:

1.) Entry into Startups:

  • How Paul came to found Highlight in the early days of consumer social?
  • What elements worked with Highlight that he took with him to Clubhouse? Which elements did not work that he learned from?

2.) Clubhouse: What Worked:

  • What does Paul believe are the primary reasons that Clubhouse grew so fast?
  • What metrics does Paul use to determine true product-market-fit and stickiness?
  • What is good retention on Day 1, Day 7 and Day 30? How important is 12-month retention?

3.) Clubhouse: What Did Not Work:

  • COVID: Does Paul believe that Clubhouse was the COVID antidote we all needed? How sustainable is that if so? What trends make it more sustainable?
  • Live Does Not Work: How does Paul respond to Mike Mignano's comments that "live does not work"? Why does Paul believe that Clubhouse is not a content platform?
  • Quality: Does Paul agree that the quality of live is not as good as the quality of produced content? Is that a problem? If the quality is worse, what is significantly better about live?

4.) The Future of Social:

  • Does Paul agree that we are seeing the disregard of the once hailed social graph in favour of a new era of recommendation media? What does this mean for Clubhouse?
  • With the rise of the likes of BeReal, how does Paul think about the importance of authenticity in the next wave of consumer social?
  • How does Paul forsee Web3 and the next generation of consumer social being interlinked? What will it take for Web3 to break through? What are the core barriers today?
  • Does Paul agree that the best consumer social tools empower creators with Superhuman powers?

5.) Lessons on CEOship:

  • What are Paul's biggest lessons on successful company building?
  • How does Paul manage the criticism and negativity of the press personally?
  • How does Paul maintain the morale internally when the press cycle is so negative?
  • How has Paul adapted himself to gain a thicker skin and not pay as much attention?

Items Mentioned in Today's Episode:

Paul's Favourite Book: Reality Is Not What It Seems: The Journey to Quantum Gravity, Information: A History, a Theory, a Flood

Sep 23, 2022

Julio Vasconcellos is the Founder and Managing Partner @ Atlantico, one of the leading early-stage funds in Latin America. Prior to the world of venture, Julio got his break in the world of startups as Facebook’s first country lead for Brazil. Julio then went on to co-found Peixe Urbano, a company he scaled to over 1,200 employees and $100M+ in revenue. Post the sale of Peixe Urbano, Julio became an EiR @ Benchmark Capital where he met Scott Belsky. Scott and Julio went on to co-found Prefer, a Benchmark backed company transforming the future of work. If that was not enough, Julio has a stellar angel track record with prior investments in the likes of Ipsy and Quinto Andar.

In Today's Episode with Julio Vasconcellos We Discuss:

1.) Entry into Startups:

  • What are 1-2 of Julio's biggest takeaways from being Facebook's first hire in Brazil?
  • What does Julio know now that he wishes he had known at the start of his career in startups?

2.) Lessons from Scaling Peixe Urbano to $100M in Revenue:

  • How does Julio advise founders on when is the right time to launch a second product or market?
  • How does Julio advise founders on the right balance between growth and unit economics?
  • When times are tougher, should founders cut fast or cut slower? What is irreversible?
  • What are the single biggest and worst things to break in hyper-scaling?

3.) Investing: Why Not Enough Play To Win:

  • What is more important, a great market or a great founder?
  • Why do not enough VCs today play to win? If they do not play to win, what do they play to do?
  • Why is greed the number one enemy of venture returns?
  • What are the single biggest investing lessons Julio has learned from Benchmark Founder, Andy Rachleff? How have they impacted his investing mindset?
  • Why does Julio believe you can have a close relationship with founders as an angel and not a VC?
  • How did Julio's approach to investing change with the transition from angel to VC?
  • Does Julio believe that boards really add any value? If so, how?
  • What is Julio's biggest investing hit? How did it change his approach?
  • What is his biggest miss? How did that impact his mindset?

4.) The Future for LATAM:

  • Is Julio as concerned as I am by the removal of growth stage capital from the LATAM ecosytem?
  • Does this mean a higher mortality rate for LATAM companies? How does Julio advise founders?
  • How did COVID adoption of technology in LATAM fundamentally differ to the US?

Sep 21, 2022

David Lieb is one of the product OGs of the last decade. As the founder of Bump David pioneered how over 150M users shared data, contacts and more before the company was acquired by Google. At Google, David took this one step further by creating Google Photos, which he has led with immense success for the last 9 years. In the last few weeks, David announced his latest move, to join Y Combinator, one of the world's leading accelerators as a Visiting Group Partner. If that was not enough, David also has a stellar angel portfolio with the likes of Rippling, Flexport, Tally, Maven and many more.

In Today's Episode with David Lieb We Discuss:

1.) Entry into Product:

  • How did an idea at business school turn into Bump and ultimately the creation of Google Photos?
  • What are the single biggest mistakes David made with the early Bump product?
  • What does David know now that he wishes he had known at the start of Bump?

2.) Scaling the Team Alongside the Product:

  • What is product-market fit to David? What is it not?
  • What are the single biggest mistakes founders make when they think they have it?
  • What should founders do first and most importantly, when they do have it?
  • Why does David believe individual user data is more important than relying on data?

3.) Product: Art or Science:

  • Why does the description we have for product managers need to change?
  • How does David determine when to act on customer feedback vs stick to the current product plan?
  • What is the right way to do customer discovery? What questions are best to ask? Where do founders make the biggest mistakes in customer discovery?
  • Ultimately, is product more art or science? Is this changing with ever-increasing data?

4.) Product: The Process:

  • How does David conduct product reviews? What are the biggest mistakes founders and product leaders make when managing product reviews?
  • Who is invited? Who sets the agenda? Who determines who is accountable for what?
  • How do product reviews change in a world of Zoom? What is better? What is worse? What can product leaders do to build culture in remote worlds?
  • How can product leaders make everyone feel safe and comfortable to share how they feel, regardless of seniority, in product reviews?

Items Mentioned in Today's Episode:

David's Best Performing Investment: Flexport

Sep 16, 2022

Seba Kanovich is the CEO @ dlocal, the #1 payments leader with a single solution focused on Latin America and other emerging markets. In June 2021, dlocal raised $617M in their NASDAQ IPO listing valuing the company at nearly $9BN. Before their IPO, dlocal raised from some of the best including General Atlantic, Bond Capital, and Oren Zeev to name a few. Prior to dlocal, Seba was CEO @ AstroPay, a leading payment solution provider in Emerging Markets.

In Todays Episode with Seba Kanovich We Discuss:

1.) The Journey to CEO of an $8BN Company:

  • How Seba made his way to the role of CEO of an $8BN company through dinner at his mother-in-law's house?
  • What does Seba know now that he wishes he had known when he first became CEO?

2.) Leadership 101:

  • What does "high performance" in business and leadership mean?
  • How important are velocity and speed of execution in startups? When should one trade speed for quality? Where is the nuance?
  • How does Seba approach prioritization? What framework does he use to determine what to focus on?
  • How does Seba think through effective delegation? How can leaders determine what only they can do?

3.) Leadership: The Challenges and Lessons:

  • What are Seba's biggest insecurities in leadership today? How does he manage them? How have they changed over time?
  • What is the single most painful leadership lesson Seba has learned that he is also pleased to have learned?
  • What gets easier with scale as a leader? What gets harder?
  • In a scaling organization, what is the first thing to break? What can be done to mitigate this?

4.) The Funding and The IPO:

  • Why did dlocal bootstrap for 4 years instead of raise funding? How did that process change their mindset toward capital efficiency? What was good about it? What was bad?
  • What are the single biggest advantages great investors can bring to the table?
  • Why did Seba decide 2021 was the right time to go public?
  • What was the biggest surprise about going public? What is better and what is worse about being a public company?

Items Mentioned in Today's Episode:

Seba's Favourite Book: Steppenwolf by Herman Hesse

Sep 14, 2022

Eleanor Dorfman is a Sales Leader @ Retool, the company that allows you to build internal tools, remarkably fast. Prior to Retool, Eleanor joined Retool when there were only three account executives and has scaled the sales org sales to over 30 AEs, many SEs, and an entire SDR team. Before Retool, Eleanor was at Segment, where she built out the company’s customer success operations team before pivoting to creating an expansion sales team, renewals team, and a new business sales team. Finally, before Segment, Eleanor made her way into startups, starting as an unpaid intern at Clever, just four years later, Eleanor was Head of Customer Success and Solutions Engineering.

In Today's Episode with Eleanor Dorfman We Discuss:

1.) Entry into Sales from Working with the US Education Department:

  • How did Eleanor get her first role as an unpaid intern at Clever?
  • What are 1-2 of her biggest takeaways from her time at Segment?
  • What are the biggest advantages of sales reps having experience in customer success?

2.) The Sales Playbook:

  • How does Eleanor define, "a sales playbook"? When does it need to be created?
  • Does it need to be the founder who creates it or can it be a Head of Sales?
  • Is it possible to run a PLG and enterprise motion from Day 1? How does this change your sales playbook?
  • How does Eleanor advise founders on when is the right time to layer on an enterprise motion, on top of a PLG motion?

3.) Who, What and When: Building the Sales Team

  • Should founders hire a Head of Sales first or sales reps first? If sales reps, should founders always hire sales reps in two's?
  • How does Eleanor structure the hiring process for all new sales team recruits?
  • What are the clearest signals of 10x sales hires? What are red flags in the interview process?
  • How does Eleanor use demo's and case studies to determine technical ability?

4.) The First 30, 60 and 90 Days: The Onboarding:

  • What is the right structure for all new sales hires to be onboarded?
  • Why does Eleanor believe you will always hire your Head of Sales Enablement too late?
  • What are the signs that now is the right time to hire your Head of Sales Enablement?
  • What tools, materials and resources can founders provide to shorten the ramp time for new AEs?
  • What are the single biggest mistakes founders make in the onboarding of new sales reps?


Sep 12, 2022

Will Quist is a Partner @ Slow Ventures. Over the last decade, the team at Slow Ventures have invested in the earliest rounds of over 500 companies including Robinhood, NextDoor, Airtable, Solana and many more. As for Will, prior to Slow he spent over 8 years at Industry Ventures and before industry, cut his teeth in the world of finance at Banc of America.

In Todays Episode with Will Quist We Discuss:

1.) Entry into Venture:

  • How Will made his way from 6th generation San Francisco to Partner @ Slow?
  • What are 1-2 of the biggest takeaways from his early 1-1s with Don Valentine?
  • What does Will know now that he wishes he had known when he started in venture with Industry?

2.) WTF Really is Venture Capital?

  • Why does Will believe that 95% of venture capital today is not really venture capital?
  • What is true venture capital in Will's mind?
  • How does Will divide the world of VC into two with; venture classic and new venture?
  • How are they different? How are their return profiles different?

3.) The Questions: Discovering Greatness:

  • Why does Will believe “for the most part, investors across asset classes are just asking the same questions”?
  • What are those questions? What different answers are each looking for?
  • What are the 5 core questions that will needs to understand to determine conviction and accurately price an asset?
  • How does Will think through and analyze the question when meeting founders of; “what needs to come true for this business to become a great business”?

4.) The Future of Venture Capital:

  • How does Will predict the venture capital ecosystem will look in 5 and then 10 years?
  • What are the most concerning traits of the venture ecosystem for Will today?
  • Who will be the winners of the next decade? Who will be the losers?
  • What happens to the crossover funds? What will happen to Tiger?

Sep 7, 2022

Mike Mignano is a Partner @ Lightspeed, one of the most successful venture firms of the last decade with a portfolio including the likes of Snap, Affirm, Epic Games, Mulesoft and more. As for Mike, prior to venture, he was Head of Talk for Spotify where he led the podcast, live, and video businesses for the world’s leading audio streaming platform. Michael came to Spotify through their acquisition of Anchor, a company he co-founded and is credited for democratizing podcasting globally. Mike has also been a prolific angel investor with a portfolio including Cameo, Pipe, Sandbox VR and Stir.

In Today's Episode with Mike Mignano We Discuss:

1.) Exclusive News:

  • What exclusive news does Mike have to share today?
  • What would Mike most like to change about the way founders experience the product of venture capital? How can VCs be better?
  • What is Mike most nervous about in the new role?

2.) The World of Social is Changing Forever:

  • Why does Mike believe there has never been a better time for the next social media giant to be born?
  • Why are the largest social giants leaving behind the social graph?
  • What is recommendation media? Why is it a better business model?
  • How does the shift from social graph to recommendation media change the way large social giants operate and interact today?

3.) Startups: Risers, Fallers and Is There Room For Another Giant?

  • What does Mike believe Clubhouse did well? What was their undoing?
  • Does Mike believe BeReal is defensible? What features make it both sticky and defensible?
  • Will TikTok be a $2 trillion dollar company? Will Meta catch TikTok or have they gone too far ahead?
  • Will OpenSea be able to sustain and make the market for NFTs, despite crypto crashing?
  • Should startups be concerned about large social giants "copying" their features?
  • What does true defensibility look like in consumer social today?

4.) Angel Investing: Hits, Misses and Lessons:

  • From writing over 50 angel checks, what are the single biggest lessons Mike has learned?
  • What has been his biggest hit? How did that change the way he thinks about investing?
  • What has been his biggest miss? In what way did that change how he invests?
  • What advice does Mike give to all angel investors looking to invest today?

Sep 2, 2022

Rene Haas is the CEO @ Arm. The technologies that Arm creates are used in over 230+ Bn devices with everything from sensors to smartphones to servers. In 2016 Softbank made Arm it's largest ever acquisition with a reported price of $32Bn. As for Rene, he was appointed CEO in February 2022 having spent the last 8 years in numerous different roles within the company. Before Arm, Rene was Vice President & General Manager of the Computing Products Business Unit at Nvidia where he enjoyed a very successful 7 years with the team there.

In Today's Episode with Rene Haas We Discuss:

1.) Entry into Tech from Eastman Kodak:

  • How did Rene make his way into the world of technology and innovation?
  • What are 1-2 of the biggest takeaways from his 7 years at Nvidia?
  • How did working with Jensen impact his leadership approach and philosophy?

2.) Decision-Making in Leadership:

  • What is the single biggest mistake leaders make when making decisions today?
  • How does Rene balance the trade-off between speed vs quality of decision?
  • At what point does Rene believe leaders have enough data to make a decision?
  • What does Rene know now that he wishes he had known when he started on decisions?

3.) Scaling the Org and Remaining Nimble:

  • Agile: How does one retain the speed and agility of a startup when one is the size that Arm is today?
  • Ambition: How does Rene as a leader inspire the same level of ambition and vision in his team when Arm is as large as it is?
  • Risk: How does Rene encourage his teams to take large risks when they have so much more to lose?
  • Breakage: What are the first things to break in scaling? What can leaders do to get ahead of them?

4.) Leadership 101:

  • What really is strategy? What is it not? What mistakes do all leaders make when it comes to strategy?
  • How does Rene define "high performance" in leadership? How has his style of leadership changed over time?
  • How does Rene approach vulnerability in leadership? What are the pros and cons?


Aug 31, 2022

Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. The company now has over 10M users around the world and over 50,000 companies loving the product. As for Annie, before Calendly, Annie led Glassdoor's product vision and user experience, managing a 70 person product and design org. Prior to Glassdoor, Annie led enterprise product teams at Box both before and after their 2015 IPO. If this was not enough, Annie is also on the Board of WorkRamp and Well Health.

In Today's Episode with Annie Pearl We Discuss:

1.) Entry into Product From Consulting:

  • How did Annie make her way into the world of product and come to lead product teams at Box and GlassDoor?
  • What are 1-2 of her biggest takeaways from her time at Box and GlassDoor? How did they impact her product mindset?
  • What does Annie know now that she wishes she had known when she started in product?

2.) PLG vs Enterprise: What, When, How:

  • Is it possible to do PLG and top-down enterprise strategy together from Day 1?
  • Why does every PLG company eventually have to adopt an enterprise strategy?
  • What are the single biggest challenges companies face when moving to enterprise?
  • How do founders know when is the right time to make this transition?
  • How do founders need to restructure their org to make the transition to enterprise?

3.) Building the Product Bench: Hiring:

  • When is the right time to hire your first product leader? What are the core signals?
  • What are the core character traits needed for a first product leader?
  • How do we specifically structure the interview to test for them?
  • Who do we bring into the interview process from other parts of the org?
  • Do we do case studies with candidates? If so, how long do they have with the data? What is the difference between good vs great with case studies?

4.) Product Strategy, Reviews and Alignment:

  • How does Annie assess how often product strategy should be reviewed? When should it change?
  • How does Annie approach post-mortems? What is the right way to structure them?
  • How does Annie create alignment between sales and product? Why is this so important?
  • What is the single biggest product mistake Annie has made? What did she learn?

Aug 29, 2022

Logan Bartlett is a Managing Director @ Redpoint, a firm with a portfolio including the likes of Stripe, Nubank, Twilio, Netflix, Snowflake and many more incredible names. As for Logan, at Redpoint he has led investments in the likes of Ramp, Monte Carlo, Cribl, Crossbeam and Acuity MD to name a few. Before joining Redpoint, Logan spent over 5 years with the team at Battery where he made investments in Pendo, Amplitude, Dataiku, Braze and Kustomer.

In Today's Episode with Logan Bartlett We Discuss:

1.) Entry into Venture:

  • How Logan made his way into the world of venture joining Battery Ventures?
  • What are 1-2 of Logan's biggest takeaways from his time with Battery?
  • What does Logan know now that he wishes he had known when he started in venture?

2.) The Venture Landscape Today:

  • Is now really the best time to be investing? How does Logan compare today to prior vintages? How does this differ when comparing consumer to B2B?
  • How does Logan analyze the state of the growth market? Is anyone really doing deals today? If so, what is the discount on price vs last year?
  • How do the public markets impact the later stage financings which have disappeared in the last 3 months? How do the later stage financings impact the early stage?
  • Does Logan agree that "venture has never been less collaborative as it is today"?

3.) The Role of the Venture Investor:

  • Why does Logan believe that VCs have gotten lazy over the last 2 years? Does Logan believe we will see even more GPs at the top retire in the downturn?
  • How does Logan analyse his role as a board member today? How has his style changed over time?
  • What is the single best board Logan is on? Why that one? Who is the best board member Logan works with? What makes this board member so good?
  • How does Logan assess the importance of personal brand in venture today? Why does Logan believe no company should hire PR firms from the early days?

4.) Investing Style and Lessons:

  • What has been Logan's single biggest hit as an investor? How did seeing that impact his mindset?
  • What has been Logan's biggest miss? How did not doing the investment change how he thinks about making new investments today?
  • How does Logan assess his own relationship to price? How has it changed over time?
  • As a growth investor today, how important is ownership? How does this change with stage?

Items Mentioned in Today's Episode:

Logan's Favourite Book: Team of Rivals: The Political Genius of Abraham Lincoln

Logan's Most Recent Investment: AcuityMD

Aug 26, 2022

Whitney Wolfe Herd is the Founder and CEO @ Bumble, changing the way people date, find friends, and the perception of meeting online, for the better. Women make the first move. Over an incredible 6 year journey, Whitney has scaled Bumble to a community of over 100 million across six continents. Bumble has facilitated an incredible 1.8 billion first moves as of 2021 and so many more by now. Prior to founding Bumble, Whitney was the Co-Founder and VP of Marketing @ Tinder.

In Todays Episode with Whitney Wolfe Herd We Discuss:

1.) Founding Bumble:

  • How Whitney made her way into the world of startups with her co-founding Tinder?
  • What happened when Whitney left Tinder in a very public way?
  • How did that and the scrutiny that came with it, impact her? How did she change?

2.) CEOship 101:

  • What does "High Performance" mean to Whitney?
  • What are the biggest benefits and biggest downside of transparency? What are the few things that as a leader, you cannot be transparent about them?
  • What does it mean to truly listen as a leader? What are the biggest mistakes leaders make when it comes to listening?

3.) Risk and Pressure in Leadership:

  • What is the single moment of highest pressure Whitney has been through in the Bumble journey?
  • How does Whitney deal with pressure as a leader today? How has that changed?
  • How does Whitney approach risk as a leader today? What is too risky?
  • How does Whitney think through her own decision-making framework?

4.) Whitney: The Mother and Wife

  • What does Whitney believe makes a truly successful marriage?
  • How does Whitney not lose an inch of performance as a public markets CEO and also be an amazing mother to two children under the age of 2?
  • What does Whitney know now that she wishes she had known when she started Bumble?
  • As a leader and mother, what gets easier with time, what gets harder?

Items Mentioned in Today's Episode with Whitney:

Whitney's Favourite Book: Shantaram

Aug 24, 2022

Over the last 7 years, I have scaled 20VC to 100M+ downloads, and listeners in 117 countries, and all of this with a spend of less than $1,000. Here are 10 of my biggest lessons:

Lesson 1: Persistence: This is a game of who can last the longest.

Lesson 2: Platform Selection: Choose the platform that best aligns to your skills and passion, not the one that is "hottest" at the time.

Lesson 3: Just Start: The biggest reason people fail is because they do not take the first step. The V1 will never be perfect but it will improve. Press publish.

Lesson 4: Consistency: You have to create a habit within your audience. You have to let them know when they should expect your content. This will also creating a forcing function for you to stick to.

Lesson 5: Be Targeted on your Content Topic: Do not be vague. You have to be very specific in the topic you choose. Start very niche. Find your 100 true fans. Expand from there.

Lesson 6: Every Piece of Content is Born Multi-Channel: You do a talk. This is not a single talk. This can be turned into a podcast. Several TikToks. A medium piece. No content is in isolation.

Lesson 7: The Right Ratio Between Creation and Distribution: Do not create content and then press publish and think the work ends there. You have to spend the same amount of time distributing the content as you do creating it.

Lesson 8: Create Champions: In the early days it is all about finding your 100 true fans. DM people that follow you. Make them feel special. They will retain and tell their friends. Create champions.

Lesson 9: Bring People Into the Creation Process: When people feel a part of the creation of content, they will share it actively. Make more people feel part of the creation process.

Lesson 10: Each Channel is Different, Optimise for Them: Different channels require different content types, formats, audio, optimise on a per channel basis.

Aug 22, 2022

Wes Chan is the Co-Founder and Managing Partner at FPV Ventures, a $450M early-stage fund, launched earlier this year. Wes is an investor in five $10B+ "decacorns," his most notable being Canva where he is a member of the board of directors and led the Series A and C rounds. Wes also wrote the first or very early check into Plaid, Flexport, Gusto, Lucid, and RobinHood. Before FPV Wes was a Managing Director at Felicis Ventures and before Felicis Wes founded GV’s seed investing program. If that was not enough, as an operator, Wes co-founded Google Analytics and Google Voice and holds 18 US patents for his work in creating Google AdWords.

In Today's Episode with Wes Chan

1.) From Founding Google Analytics to Venture:

  • How did Wes make his way from founding Google Voice and Google Analytics to starting GV's seed investing program?
  • What are 1-2 of the single biggest product takeaways from working closely with Larry and Sergey @ Google?
  • How did Wes make his way from Google to Felicis and scaling the firm with Aydin Senkut?

2.) Market vs Founder: Why Market Sizing is BS:

  • Why does Wes believe that the market always wins over the founder?
  • That said, what does Wes mean when he says "the best founders have 100 year plans?"
  • How does Wes question and analyse 100 year plans? What makes the best? What makes the worst?
  • Why does Wes not do market sizing? Why does Wes not do outcome scenario planning?
  • What does Wes believe is the biggest fallacy of outcome scenario planning?

3.) The Venture Landscape:

  • Does Wes believe that now is really the best time to be investing?
  • Why does Wes believe there are some treacherous deals being done now? What are the signs that these deals are challenging?
  • What advice does Wes give founders fundraising in these markets?
  • What does Wes believe are elements that traditional VCs decide to do, which prevents founders from choosing to work with them?
  • Does Wes believe VCs on board truly provide value? If so, which ones and why them?

4.) FPV: Firm Building and Portfolio Construction:

  • With the new $450M fund, what is the portfolio construction that Wes chose?
  • Why does Wes prefer to have more lines in the portfolio than a concentrated portfolio?
  • Does Wes believe you can increase your ownership in your best companies over time?
  • How does Wes think about capital concentration on a per company basis?
  • What have been Wes' biggest lessons from his biggest hits and misses?

Items Mentioned in Todays Episode:

Wes' Favourite Book: Liar's Poker

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