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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Jun 17, 2022

Nick Jones is the Founder & CEO @ Soho House, it all started in 1995 when Nick opened the first location above his restaurant, Cafe Boheme, a members’ club for the local artists and actors of London. Today, Soho House is a global brand, a private members club that includes 33 Houses in 14 countries, with more openings in Europe, Asia, and North America on the horizon. In 2021, Nick took Soho House public on the NASDAQ, 25 years since opening the first location. If that was not enough, Nick is also the owner of Babbington House and Cecconi's, one of my favorite restaurants in London.

In Today's Episode with Nick Jones You Will Learn:

1.) The Start of Soho House:

  • What was the founding moment for Nick with Soho House?
  • What were the biggest lessons from his 3 prior restaurants not working? How did that experience change his approach to Soho House?
  • Why does Nick believe resilience is the most important skill of any entrepreneur? When something is not working? What does Nick tell himself?
  • With the rise of Instagram, how have the demands of the consumer changed over time in terms of what they expect from hospitality?

2.) The Art of Storytelling:

  • What does Nick believe is the essence of truly great storytelling?
  • What do all great stories contain? How do the best storytellers tell those stories?
  • Where does Nick believe many founders make mistakes when it comes to storytelling today?

3.) The Art of Leadership:

  • How does Nick define his style of leadership today? How has it changed over time?
  • What does high performance mean to Nick?
  • How does Nick think through retaining high performance while also having a family?
  • How does Nick approach hiring? Why does Nick find interviewing so tough?
  • How does Nick think through when to hire someone external vs promote internal talent?

4.) The Scale of Soho House:

  • What was the single most challenging time in the scaling journey of Soho House?
  • What changes when you go public? What are the good? What are the bad?
  • What does Nick know now that he wishes he had known in the beginning?

Jun 15, 2022

Adam Fishman is one of the leading growth practitioners of the last decade. Most recently, Adam was the Chief Product and Growth Offer at Imperfect Foods, where Adam built a 40-person product and growth organization, responsible for 70% of overall company metrics and growing revenue by 400% in one year to $600M annually. Before Imperfect, Adam spent 4 years as VP of Product and Growth @ Patreon, driving the company pivot and rebrand and helping the company scale to $1BN GMV and $100M in revenue. Finally, before Patreon, Adam was the Head of Growth @ Lyft, Adam was the first growth and marketing employee hired, grew the team to 18 people, and reported directly to the founders.

In Today's Episode with Adam You Will Learn:

1.) Entry into Growth:

  • How Adam first made his way into the world of growth when "growth" did not exist as a function?
  • What were Adam's biggest lessons from leading Lyft's growth team? How did that impact his mindset?
  • What are some of Adam's biggest takeaways from his time at Patreon? What are some of the biggest mistakes he made at Patreon?

2.) The Basics: Growth 101: What and When:

  • How does Adam define "growth" today? What is it? What is it not?
  • When is the right time to hire your first growth hires?
  • Should this first hire be a seasoned growth leader or a more junior growth rep?
  • What characteristics and skill sets should this growth hire have?

3.) The Hiring Process:

  • How should founders structure the hiring process for their first growth hire?
  • What 3 questions should all founders ask in the hiring process for growth?
  • How can founders use data and case studies to really test the skillsets of growth candidates?
  • Why does Adam believe that the hiring process for growth and product is so broken?

4.) The Onboarding Process:

  • What is the right way to structure the onboarding process for new growth hires?
  • How should growth hires create cross-functional relationships and communication with the rest of the team? What has worked for Adam in the past? What has not?
  • What are the signs that are new growth hire is not working? How long should they be given?
  • What are the signs that are a new growth hire is working? What is the sign of "exceptional"?

5.) Adam Fishman: AMA:

  • What growth decision has Adam made without data? How did it go?
  • How does Adam define "viral loops"? What makes one better than another? Where do so many make mistakes with viral loops?
  • Adam led the rebrand for Patreon, what is the secret to a successful rebrand? What are some of the most common pitfalls to avoid?

Items Mentioned in Today's Episode with Adam Fishman

Adam's Favourite Book: First 90 Days, Critical Success Strategies for New Leaders at All Levels

Jun 13, 2022

Dharmesh Shah is the Founder and CTO @ Hubspot, a full CRM platform with marketing, sales, service, and CMS software. Dharmesh started Hubspot in 2006 and today it is a publicly-traded company (NYSE: HUBS) with over 3,500+ people and a market capitalization of $16.9 billion. Prior to founding HubSpot, Dharmesh founded Pyramid Digital Solutions, which he bootstrapped with less than $10,000 and after 11 years of CEOship, Dharmesh helped the company get acquired in 2005 by SunGard Business Systems. In addition to co-authoring “Inbound Marketing" Dharmesh founded and writes for -- a top-ranking startup blog and community with more than 1,000,000 members. Finally, if all of this was not enough, he is an angel investor in over 90 startups, including Coinbase, AngelList, Gusto, Okta and many more. and a frequent speaker on startups, growth, and the business of technology.

In Today's Episode with Dharmesh Shah We Discuss:

1.) The Founding of Hubspot:

  • How did Dharmesh's wife help Dharmesh find his co-founder in Brian?
  • What about SMB did both Dharmesh and Brian find a shared passion for?
  • What is the single biggest mistake Dharmesh made in the early days of Hubspot?

2.) The Culture Code:

  • What is Dharmesh's single biggest advice to founders when it comes to culture?
  • What does Dharmesh mean when he says "you have to treat culture like a product"?
  • What does Dharmesh mean when he says he looks for a "low ego to accomplishment ratio"? How does he test for this when hiring new hires?
  • How do the best people approach both responsibility and accountability? How does this show in their work and behaviour?

3.) The 3 Kinds of Risk in Startups:

  • What does Dharmesh believe are the 3 core risks all startups face in the early days?
  • How does Dharmesh advise founders when it comes to "testing for a market"? What is the right way to do customer discovery? What are the biggest mistakes founders make in the discovery process?
  • How does Dharmesh advise founders on when to release their second product? What is the right framework for this decision? Where do so many founders make mistakes here?
  • How does Dharmesh approach market timing risk? What have been his biggest lessons here?

4.) SMB vs Enterprise:

  • Why does Dharmesh believe that SMB is the single best market for founders to choose?
  • What are the single biggest challenges with enterprise? How do the long sales cycles and contracts in enterprise hide both customer satisfaction and prevent product development?
  • What are some of Dharmesh's biggest lessons on pricing? Does Dharmesh agree you should always "raise your prices"?
  • How does Dharmesh advise founders on when is the right time to go into enterprise from SMB?
  • What are the single biggest changes founders need to know when making the move from SMB to enterprise?

5.) Angel Investing 101:

  • What are Dharmesh's rules when it comes to angel investing?
  • What have been some of Dharmesh's biggest lessons from analysing thousands of emails to founders pre-investing? What are the biggest signs in emails of future founder success?
  • Why does Dharmesh not have calls with founders before investing?
  • What are some of the biggest mistakes Dharmesh has made when angel investing?

Items Mentioned in Today's Episode with Dharmesh Shah:

The Hubspot Culture Code

Dharmesh's Favourite Book: Les Miserables

Jun 10, 2022

Ruchi Sanghvi is a Founder and Partner @ South Park Commons Fund, a home for the most talented technologists, builders, and domain experts figuring out what's next. Prior to SPC, Ruchi was the first female executive at Dropbox and served as their Vice President of Operations. Prior to Dropbox, Ruchi was the first female engineer at Facebook, and was instrumental in implementing the first versions of key features like News Feed, Facebook Platform, Facebook Connect and Privacy. Ruchi has also served as a director on the board of Paytm, India’s largest mobile payments platform. Prior to SPC, Ruchi was an active angel investor in 50+ companies including Gusto, Pinterest, Paytm, Brex, Figma, and Stemcentrx.

In Today's Episode with Ruchi Sanghvi:

1.) From First Female Engineer To Community Leader and Fund Manager:

  • How Ruchi made her way into the world of tech becoming the first female engineer at Facebook?
  • What were her biggest lessons from her time at Facebook?
  • What does Ruchi believe makes Mark Zuckerberg the special leader he is?
  • How did Ruchi's time at Dropbox impact how she operates today?
  • Does Ruchi agree with the Facebook motto, "move fast and break things"?

2.) Answering Life's Big Questions: Ego, Money, and Insecurity:

  • What advice did Ruchi's father give her before he passed away that really impacted how Ruchi operates and acts in the world today?
  • How does Ruchi assess her own relationship to money? How has it changed over time? How does she use a spreadsheet to measure her relationship to money?
  • Having had such success so young, how does Ruchi approach ego management? When has Ruchi been arrogant in the past? How does she manage her ego today?
  • What are Ruchi's biggest insecurities today? Why are they?

3.) Will DAOs Replace Venture Capital:

  • How does Ruchi analyze the crypto fund landscape today? Where are the opportunities?
  • Does Ruchi believe that large multi-stage firms can simply hire crypto partners and win in the new world of Web3 and crypto?
  • How does Ruchi believe DAOs will disrupt the venture model today? Will DAOs displace institutional LP dollars from venture funds and be directed to DAOs?
  • How are DAOs governed today? Who makes the decisions? How are tokens allocated?

4.) -1 to Zero: The Art of the Pick:

  • What does Ruchi mean when she speaks of -1 to zero? What stage of company formation is this?
  • What is the right framework by which founders should approach picking an idea to work on?
  • How should a founder know when to give up and try a new idea?
  • What are the most common mistakes founders make in this stage of idea picking?

Jun 8, 2022

Kayvon Beykpour is one of the most prominent product leaders of the last decade. For the last 7 years, Kayvon has been at Twitter where he led all of the teams across Product, Engineering, Design, Research and Customer Service & Operations. Kayvon came to Twitter through Periscope, the live broadcasting app that raised from GV, Bessemer, Scott Belsky and was ultimately acquired by Twitter in 2015. If that was not enough, Kayvon is also an active angel investor today.

In Today's Episode with Kayvon Beykpour You Will Learn:

1.) Entry into Product:

  • How did Kayvon make his way into the world of tech and come to be Head of Consumer Product @ Twitter?
  • What were some of Kayvon's biggest lessons from the journey with Periscope?
  • What were some of Kayvon's biggest takeaways from working closely with Scott Belsky?

2.) Building Your Product Team:

  • How does Kayvon advise on your first product hires? Should it be Head of Product or more junior product team members?
  • When is the right time for the founder to hand off some core product decisions to these hires?
  • What are the core traits and characteristics of some of the best first product hires?

3.) Perfecting the Hiring Process for Product Teams:

  • How does Kayvon approach the hiring process for all new product team members?
  • What are the stages? What does he look to learn at each stage?
  • What questions reveal the most in product candidates? How do the best respond?
  • How does Kayvon use case studies and product demos in the process?

4.) Building Product: 101:

  • How does Kayvon approach product reviews? Who is invited? Who sets the agenda? How often?
  • What have been Kayvon's biggest lessons about what leaders need to do to get the most from their product teams? How do they communicate?
  • What has been one of Kayvon's biggest product mistakes? What did he learn?
  • How does Kayvon advise founders on when to give up on a new product vs when to iterate and persist?

Jun 6, 2022

Ian Lee is the Co-Founder of Syndicate, a web3 startup that has raised over $28M from a16z, Kleiner Perkins, IDEO, and 300+ investors. Previously, Ian was Managing Partner of IDEO CoLab Ventures, a crypto venture fund backed by IDEO focused on web3, crypto, and blockchain startups. From 2017-2021, Ian led investments and helped incubate 80+ crypto startups in the areas of DeFi, NFTs, DAOs, and more. From 2014-2017, Ian was the Head of Crypto at Citigroup and Citi Ventures globally. Listen to our prior episode on DAOs with Avichal Garg here.

In Today's Episode with Ian Lee We Discuss:

1.) Ian's Entry into Tech and Crypto:

  • Why did Ian decide early on that he did not like being a VC?
  • What was it that changed his mind, showing him the impact investing can have?
  • What have been the most significant but non-obvious developments in crypto?

2.) Why DAOs Will Replace Venture Capital:

  • Why does Ian believe that DAOs will replace venture capital firms over time?
  • How does Ian analyze the current landscape of Web3 investing and VC?
  • Can existing firms layer on a Web3 Partner or Fund and win in the new Web3 landscape?
  • How will the next generation of Web3 native firms be structured?

3.) DAOs 101:

  • What really is a DAO? What is not a DAO?
  • How are DAOs structured? How many people are invited? Who decides who is invited?
  • How are decisions made within DAOs? How does this differ dependent on structure?
  • What are the single biggest challenges that DAOs face today in operations?

4.) Crypto is The Future of the Internet:

  • What does Ian mean when he says "crypto is the future of the internet"?
  • What does this mean for the distribution of ownership and wealth in the next generation of the internet?
  • Do DAOs and Web3 do more to harm or hurt income inequality today?
  • What are the drivers that would lead Web3 to centralize wealth even further?

Items Mentioned in Today's Episode with Ian Lee:

Ian's Fave Book: The Innovator's Dilemma: The Revolutionary Book That Will Change the Way You Do Business

Ian's Fave Web3 Resources: a16z's Crypto Canon, Jesse Walden's: The Ownership Economy 2022

Jun 1, 2022

Over the last 10 days, we have seen unprecedented levels of layoffs from some of the biggest quick commerce providers in the world from Getir to GoPuff to Zapp and Gorillas. Today we dive into the world of quick commerce in emerging markets to uncover what is the same and what is different about the model in emerging markets.

Usman Gul is the Founder & CEO @ Airlift, one of the fastest-growing quick commerce providers in the world with core operations in Pakistan. Airlift has raised over $100M in funding from First Round, Josh Buckley, Sam Altman, and 20VC.

Ralf Wenzel is the Founder & CEO @ JOKR, a unique provider in the quick commerce market with their dual operations in both the US and LATAM. They are one of the only providers to operate in both emerging and developed economies. To date, JOKR has raised over $288M from Softbank, Balderton, GGV, and Kaszek to name a few.

Aadit Palicha is the Founder & CEO @ Zepto, they have taken the Indian quick commerce market by storm since their early days in YC. To date, Aadit has raised over $360M with Zepto from YC, Lachy Groom, Breyer Capital, and Rocket Internet to name a few.

In Today's Episode on Quick Commerce in Emerging Markets You Will Learn:

1.) Emerging Markets vs Developed Economies: Where is Quick Commerce Best?

  • What are the single biggest benefits for quick commerce providers in emerging markets?
  • What are the single biggest challenges of operating quick commerce companies in emerging markets as compared to developed economies?
  • From a cost of goods and delivery perspective, what is the single biggest difference comparing operating in emerging markets?

2.) Warehouses, Picking and Delivery: The Economics Broken Down:

  • What % of revenue does Zepto, Airlift and JOKR spend on average for new warehouses in mature markets? How does this change over time? How do they select warehouse locations?
  • What % of revenue is picking costs for Zepto, Airlift and JOKR? What are some needle moving things that could reduce this picking cost?
  • What % of revenue is delivery costs for Zepto, Airlift and JOKR? What levers can make this driver efficiency and delivery cost more efficient?
  • What % of AOV does Airlift and Zepto charge for delivery? How does Zepto leverage power users to subsidise the delivery costs for newly acquired users?
  • Why does JOKR not agree with charging delivery fees? How does charging delivery fees impact usage, frequency and AOV?

3.) Product Selection and Margins: Who Goods Have The Highest Margins?

  • How do Zepto, Airlift and JOKR select the products they sell? How do the margins differ across different product categories?
  • Why is fruit and vegetable the most important category for all three providers? What other metrics are heavily impacted by large spend on fruit and vegetable spend?

4.) AOV and Customer Spend: What is Good?

  • What is the AOV for Airlift, JOKR and Zepto today? How do new markets compare to more mature markets? What are the drivers of the increase?
  • Why does Zepto not believe that AOV is the right metric to be tracking? Why is gross profit per order the right metric to be tracking?

5.) Additional Business Models: Advertising:

  • How much revenue does JOKR, Airlift and Zepto make from advertising revenue today?
  • What can be done to increase this?
  • How have JOKR been able to scale advertising revenue in such a short space of time? What has worked? What has not worked?
  • How important is advertising revenue to the future sustainability of the business model?

May 30, 2022

Keith Rabois is a General Partner @ Founders Fund, one of the best performing funds of the last decade with a portfolio including Facebook, Airbnb, SpaceX, Stripe, Anduril, the list goes on. As for Keith, he has led the first institutional investments in DoorDash, Affirm and co-founded Opendoor. He has also led investments in Faire, Ramp, Trade Republic, and Stripe. As an operator, Keith has an unparalleled track record as a Senior Exec at Paypal, he then went on to influential roles at Linkedin and being COO at Square. Finally, as an angel, Keith made early investments into Airbnb, Lyft, Palantir, Wish and more.

In Today's Episode with Keith Rabois:

1.) Buy Low, Sell High: What BS!

  • Why does Keith believe that "buy low, sell high" does not work in venture?
  • Why would it lead you to very dangerous investment decisions at the early stage?
  • How does the size of your fund impact the appropriateness of "buy low, sell high"?

2.) The Current Landscape:

  • Does Keith believe the current state of public markets is an over-reaction or a new normal?
  • How does Keith respond to the suggestion that Founders Fund has paused new investments given the uncertainty in the market?
  • How does Keith think about investing through cycles and temporal diversification?
  • How does Keith advise young investors today questioning whether they are actually any good at this?
  • What does Keith believe are his biggest fears and insecurities today?

3.) Outcome Scenario Planning and Competitor Analysis:

  • Does Keith believe outcome scenario planning is important?
  • Why does Keith believe you can always tell your biggest hits early? What have been the core signs for him?
  • What have been some of Keith's biggest lessons from Mike Moritz and Vinod Khosla when it comes to upside maximization? What are the right questions to ask?
  • Why does Keith believe you do need to look through public market comps when investing in startups?

4.) Time Allocation and Losing Faith in Founders:

  • How does Keith approach time allocation across the portfolio? Spend time with the winners or help the struggling companies? What have been his biggest lessons here?
  • What does Keith do when he has lost faith in the founder? How does he communicate it to them?
  • What does Kieth believe VCs do wrong when they no longer believe in the founder or company?

5.) Do VCs Add Value?

  • What does Keith believe is the acid test for whether he is doing his job as a VC properly?
  • Why does Keith believe there are only 5 board members that add true value to their companies at scale?
  • Who is the best board member Keith has ever worked with? Why?
  • Why does Keith believe that age is not your friend as an investor? How does he combat this?

6.) The Downfall of SF and Wokeness:

  • Will we see a reduction of wokeness in companies with the public markets correcting and power shifting from employees to employers?
  • Is Keith concerned by the lack of coherence in the US today when it comes to politics?
  • What are the core reasons for the downfall of SF to Keith?
  • Why does he believe it is a net negative to build a company in SF today?

Items Mentioned in Today's Episode:

Keith's Most Recent Investment: Found

May 27, 2022

Aydin Senkut is the Founder and Managing Partner of Felicis. An original super angel turned multi-stage investor, he has been named on the Forbes Midas List for the past nine years (2014-2022). Felicis has been an incredible 16-year journey starting with a $4M Fund I back in 2006, their most recent fund in 2021 was $900M. Along the way, Felicis has invested in over 45 unicorns including Adyen, Canva, Shopify, Notion, Opendoor, and Plaid. Prior to starting Felicis, Aydin was a Senior Manager at Google where he spent an incredible 6 years.

In Today’s Episode with Aydin Senkut:

1.) The Founding of Felicis:

  • How did Aydin transition from a successful angel to the first $41M institutional fund with Felicis?
  • How did Aydin's mindset change moving from investing personal to LP capital?
  • What does Aydin know now that he wishes he had known when he started Fund I?

2.) Fund Mechanics: Building a Portfolio

  • Why does Aydin believe portfolios need to have 40-50 positions to be diversified enough?
  • Given Aydin being multi-stage, how important is ownership on first check for Aydin and Felicis?
  • Does Aydin believe it is possible to really concentrate capital into your best performers?
  • How does Aydin think through outcome scenario planning? What is his biggest takeaway from this?

3.) Aydin Senkut: The Investor

  • What have been the biggest changes in Aydin's style of investing over the last 16 years?
  • What was Aydin's biggest miss? How did it impact his mindset moving forward?
  • What is Aydin's biggest insecurity as an investor today? How has it changed?
  • Where does Aydin still believe he is weak as an investor? What is he doing to combat it?

4.) The Venture Landscape:

  • Why does Aydin believe that despite the pricing, seed is the best risk-adjusted asset class?
  • How does Aydin evaluate where crossover funds will move with the death of many growth rounds?
  • What segment of the market will be hit hardest by the crunch? What worries with this?
  • What would Aydin most like to change about the venture landscape today? Why?

Item’s Mentioned In Today’s Episode with Aydin Senkut

Aydin’s Favourite Book: The Black Swan: The Impact of the Highly Improbable

May 25, 2022

Oliver Jay (OJ) is one of the most successful sales leaders of the last decade. Most recently, OJ spent 6 years at Asana where he was hired as the company's first revenue leader. As CRO, OJ was responsible for product-led and sales-led revenue and grew the team from less than 20 to over 450. Before Asana, OJ spent 4 years at Dropbox in a period of hyper-scaling for the business where OJ was Head of APAC and LATAM. At Dropbox, OJ scaled the sales team from 0 to 50 while tripling ARR. If that was not enough, OJ is also an independent board member at Grab, the leading Super app in Southeast Asia.

In Today’s Episode with Oliver Jay You Will Learn:

1.) Entry into Sales:

  • How did OJ make his way into sales with Dropbox?
  • If OJ were to choose 1-2 lessons from his time at Dropbox and Asana that have stayed with him, what would they be? How did they impact his mindset?
  • What were some of the non-obvious but crucial things Asana and Dropbox did in sales that led to success?

2.) The Playbook:

  • Why does OG disagree with so many definitions of "the sales playbook"? What is the sales playbook to OJ? What are the different chapters?
  • Should the founder be the one to create the sales playbook?
  • What are the signs that the founder has a repeatable and scalable playbook?
  • When is the right time to hire the first sales rep? Should it be a Head of Sales or Sales Rep?
  • How does the first hire depend on whether you are PLG or enterprise sales led?

3.) The Hiring Process:

  • How does OJ structure the hiring process?
  • How does OJ know the qualities that he wants to uncover in each candidate?
  • What questions does OJ ask to unpack whether the candidate has those qualities?
  • How does this differ when hiring sales reps vs sales leaders?
  • How does OJ use the sales demo to test the quality of a candidate? What does he want to see?
  • Who does OJ bring into the interview process? When do they get involved?
  • What are two questions that will immediately tell whether someone is a good manager?

4.) Sales Onboarding:

  • How does OJ segment sales onboarding into 3 crucial steps?
  • Chapter 1: Support: Why does OJ believe it is so important for reps to spend their first week with support? What should they look to learn? What questions should they be asking?
  • Chapter 2: Market Knowledge: How can sales leaders teach and educate new reps on market landscape, dynamics and competition? Why does this have to come before sales training?
  • Chapter 3: Sales Training: In the final step, what does the sales training process? What does OJ look for in the final sales demo? When does OJ let reps speak to customers? How does this differ when comparing enterprise to PLG?

May 23, 2022

Oren Zeev is the Founding Partner @ Zeev Ventures and one of the OGs of solo capitalism. Oren has an incredible portfolio including investments in Audible, Houzz, Chegg, Riverside, Tipalti, TripActions, and Firebolt to name a few. Oren is also very unlike any other VC firm, he does not employ any associates, principals, or staff. He doesn't have partners or partner meetings. No LP meetings. No processes. No investment committees or memos. Nada. Oren is doing it differently. Prior to starting Zeev Ventures, Oren spent 12 years as a GP @ Apax Partners where he c-headed their technology practice in their Silicon Valley office.

In Today’s Episode with Oren Zeev You Will Learn:

1.) Origins into Venture:

  • How did Oren make his way into venture over 20 years ago?
  • How does the crash of today compare to the dot com and 2008? What is the same? What is different?
  • Why did Oren decide to leave Apax and start Zeev Ventures on his own?

2.) Deployment Pace:

  • Why does Oren believe that the benefits of temporal diversification are overstated?
  • Oren raised 3 funds and over $1BN in a year, how does this current environment impact how Oren thinks about deployment pace? Will he change anything?
  • How does Oren explain deployment pace to LPs who question him?

3.) Ownership:

  • How central a role does ownership play for Oren in terms of his investor psychology?
  • Does Oren believe it is possible to increase your ownership in subsequent rounds, in your best companies?
  • What are the biggest mistakes that big funds make with regards to ownership requirements?
  • Why is there a misalignment between GP and LP when it comes to increasing ownership vs markups?

4.) Price Sensitivity:

  • How does Oren evaluate his own relationship to price today?
  • What have been some of Oren's biggest lessons on price from his biggest wins and losesses?
  • What mistake do the majority of investors make when it comes to price?

5.) Diversification:

  • Why does Oren believe that both GPs and LPs are wildly over-diversified in their portfolios?
  • What is the right amount of companies for GPs to have in their portfolio?
  • How does Oren advise LPs on the right amount of funds for them to be invested with?

6.) Oren Zeev: AMA:

  • What does Oren know now that he wishes he had known when he started his career in venture?
  • What elements of the world of LPs would Oren most like to change?
  • Why does Oren feel that the concept of pro-rata is a lazy one?

Item’s Mentioned In Today’s Episode with Oren Zeev

Oren’s Most Recent Investment: Bad Blood: Secrets and Lies in a Silicon Valley Startup

May 20, 2022

Ian Siegel is the Founder and CEO @ ZipRecruiter, a leading online employment marketplace that uses AI-driven matching technology to actively connect millions of businesses and job seekers to their next great opportunity. Since co-founding the company in 2010, more than 1.8M employers have used ZipRecruiter to find their next great hire and over 500 million job applications have been submitted through the site. Prior to their IPO last year, Ian bootstrapped the company for many years to many millions in revenue before taking venture funding from IVP, Wellington Management and Basepoint Ventures to name a few. Before founding ZipRecruiter, Ian served in key leadership roles at CitySearch,, and (an eBay company).

In Today’s Episode with Ian Siegel You Will Learn:

1.) The Founding of Olo:

  • How did Ian co-found ZipRecruiter from his kitchen with no venture funding and his 3 friends?
  • Why did they decide to not raise venture funding in the early days?
  • What was the catalyst at $50M in revenue for realising now was the right time to raise funding?

2.) The Art of Great Storytelling

  • What does truly great storytelling mean to Ian? What are the components of a great story?
  • Why do so many people today f*** up their product marketing and messaging?
  • Why does Ian believe Version 1.0 is the only one that takes true courage?

3.) CEO's Do As Little As Possible

  • Why does Ian believe his job as CEO is to do as little as possible?
  • How does Ian determine between the things he, the CEO should do, vs those those he should delegate?
  • Why does Ian believe the art of leadership and the art of parenting are the same?

4.) The Art of Hiring:

  • How has Ian's approach to hiring changed over the years?
  • What does Ian mean when he says, "I look for pointy people"? How does he detect them?
  • What are the two qualities that make the best execs? What questions reveal them?

5.) Parenting and Marriage:

  • Does Ian worry that with increasing family commitments, he loses an inch on work?
  • Why does he believe he is in an advantage as a CEO to those that do not have children?
  • What was the biggest argument he has had with his wife? How did it change his perspective?

Item’s Mentioned In Today’s Episode with Ian Siegel

Ian’s Favourite Book: Living with a SEAL: 31 Days Training with the Toughest Man on the Planet

May 18, 2022

Darius Contractor is one of the pre-eminent growth leaders of the last decade. As a growth OG, he has been VP Growth @ Airtable, where he led the growth, engineering, and product teams. Before Airtable, Darius was Head of Product Growth @ Facebook Messenger and finally, before Facebook, Darius spent 4 years as Head of Growth Engineering at Dropbox; here, Darius helped drive Dropbox to $100M in net new revenue through Dropbox Business. If that was not enough, Darius is also an active angel and fund investor with a portfolio including Calm, Airtable, Clubhouse, Census and LP checks in Maven Ventures and Long Journey Ventures.

In Today’s Episode with Darius Contractor You Will Learn:

1.) Darius Contractor: Entry into Growth:

  • How did Darius make his way into the world of growth? What was that first entry position?
  • What are 1-2 of the biggest takeaways for Darius from his time at Airtable, Dropbox and Facebook?
  • What 1-2 pieces of advice would Darius give to a growth leader starting a new role today?

2.) When is the Right Time:

  • What does the term"growth" really mean to Darius? How do so many confuse it?
  • When is the right time to make your first growth hire as a startup?
  • Should this hire be a junior growth person or a growth leader?
  • Should this initial growth team be placed inside an existing team or as a standalone team?
  • Where do so many startups make mistakes when making this first hire?

3.) Who To Hire:

  • How does one structure the process for your first growth hire? What are the stages?
  • What are the qualities that we are looking to uncover in these first hires?
  • What are the 4 interview stages to go through to test for these qualities?
  • How should founders use case studies and practicals as a way to test for these qualities?

4.) Onboarding and Integration:

  • What does the optimal onboarding process for new growth hires look like?
  • What do the best growth hires do in the first 30/60/90 days?
  • What are some early red flags that a new hire is a mis-hire?
  • How can leaders encourage cross-functional communication between growth and the rest of the org?

May 16, 2022

David Fialkow is the Co-Founder and Managing Director @ General Catalyst, one of the leading venture firms of the last decade with a portfolio including Stripe, Snap, Airbnb, Anduril, Canva and many more amazing names. Prior to founding General Catalyst with Joel Cutler, David was a serial entrepreneur building and selling 4 successful companies.

In Today’s Episode with David Fialkow:

1.) Everything Great Starts Small:

  • How did David and Joel decide on a Hawaiin beach that they wanted to start General Catalyst?
  • Why did they decide to name it General Catalyst?
  • How did the first fundraise go for GC Fund I?

2.) Creating a Firm: The Early Days

  • What design objectives did Joel and David have when they started the firm?
  • How did Joel and David think about firm expansion; going to the West Coast? Coming to Europe? Going multi-stage? What drives their decision to do new products?
  • On reflection, what were some of the toughest elements of the early days with GC?
  • What does David believe they got right? Why? What did they get wrong? How would he change it?

3.) The Partnership:

  • What does David believe makes for a truly successful venture partnership?
  • How does a great venture partnership align to what makes a successful marriage?
  • How does David approach trust? How does he build it with people?
  • What situations would cause David to lose trust? Why do so few people understand it?
  • What does David believe is the true secret to authentic relationship building?

4.) Doing the Impossible: Generational Transition:

  • What does David believe they did so right in their generational transition at GC?
  • What do many firms get wrong in handing over the reins to the next generation?
  • What are the biggest commonalities between venture partnerships and filmmaking?

Mentioned in Today’s Episode with David Fialkow:

David’s Favourite Book: The 7 Habits Of Highly Effective People

May 11, 2022

Tony Fadell, often referred to as the father of the iPod is one of the leading product thinkers of the last 30 years as one of the makers of some of the most game-changing products in society from the iPhone and iPod to more recently founding Nest, creating the Nest Thermostat, leading to their $3.2BN acquisition by Google. Tony recently released Build, this is a masterclass taking 30 years of product and company building lessons and packaging them for you, check it out here.

In Today's Episode with Tony Fadell:

1.) Everything Great Starts Small:

  • How did Tony make his way into the world of product in the early days?
  • What were his biggest takeaways from the massive flop of General Magic?
  • How did Tony come to Apple and what were the early creation days of iPod and iPhone?

2.) Data and Brand:

  • Does Tony believe great product building is art or science? When should teams listen to their gut vs the data?
  • When was a time that Tony listened to his gut? When was a time Tony listened to the data? How did each situation evolve and turn out?
  • How does Tony think about creating a truly special first mile experience? Where do so many companies go wrong in the first mile today?
  • How does Tony balance between business decisions (COGs etc) and product decisions that will delight customers?

3.) Lessons from Steve Jobs on Product Marketing:

  • How does Tony define great product management? Why do so many people get it wrong?
  • What are Tony's biggest lessons from working with Steve Jobs on what makes great product marketing?
  • Where does Tony see so many companies make the biggest mistakes when it comes to messaging?
  • What is the difference between messaging, marketing and communications?

4.) Hiring Product Teams:

  • What are the clearest signals of the best product talent when interviewing them?
  • What questions does Tony always ask product people to determine quality?
  • How do great product teams remain upbeat when launches fail and remain modest when they are wildly successful?

5.) Apple Watch, iPod and Apple HiFi:

  • Why was the product messaging for the Apple Watch wrong in the early days? How did it change?
  • Why was the iPod a bad business until the 3rd Generation? What changed?
  • Why did the Apple HiFi fail? How did that impact Tony's mindset?

Mentioned in Today's Episode with Tony Fadell:

Tony's Favourite Book: Only the Paranoid Survive

May 9, 2022

Fabrice Grinda is the Founding Partner @ FJ Labs, with over 700 investments, Fabrice has had over 250 exits and built a portfolio including Alibaba, Coupang, Airbnb, Instacart, Flexport, and Delivery Hero, and many more. Prior to FJ Labs, Fabrice served as CEO for three multinational companies; including OLX, one of the largest websites in the world with over 300 million unique visitors per month. As a result of his incredible investing success, Fabrice was named the #1 Angel Investor in the world by Forbes.

In Today's Episode with Fabrice Grinda:

1.) Everything Great Starts Small:

  • How did Fabrice make his way into the world of investing from founding 3 companies?
  • How does Fabrice feel about founders raising funds with external LPs?
  • Why does Fabrice feel that investing as an angel made him a better CEO?

2.) WTF is Going On: The Market Today

  • How does Fabrice assess what is happening in the market today?
  • What is causing the massive public market drops we are seeing?
  • How do inflation rates and interest rates have such an impact on where we are?
  • How much of this is a result of COVID, the shift to goods from services and supply chains?

3.) The Optimistic Case:

  • How does Fabrice think things could get better from here? What needs to happen?
  • What could the Fed do to enable this optimistic outcome to take place?
  • What would need to happen in geo-politics and Russia for this to happen?
  • What is the probability today of this optimistic case happening?

4.) The Great Stagnation:

  • How does Fabrice think the economy could go sideways from here?
  • What are the core drivers of this?
  • Why is this the most likely outcome of all? What is the probability of this happening?

5.) The Catastrophe:

  • How could this market get so much worse?
  • What level of interest rate change would cause this outcome to occur?
  • Why does Fabrice think that Switzerland is a "House of Cards"? What would this mean if Switzerland fell? What other European countries does Fabrice think are vulnerable?

6.) What this Means for Venture:

  • How will LPs respond to these differing situations?
  • How does this impact how Fabrice thinks about his rate of deployment?
  • What segment of the market is Fabrice most excited for; early or growth?

Mentioned in Today's Episode with Fabrice Grinda:

Fabrice's Favourite Book: Sapiens: A Brief History of Humankind

May 6, 2022

Jason Lemkin is the Founder and Managing Partner @ SaaStr, a social community of 500,000+ SaaS founders and a $100M venture fund. In the past, Jason has made investments in the likes of Algolia, Talkdesk, Pipedrive, and RevenueCat to name a few. Prior to SaaStr, Jason was the Co-Founder and CEO @ Echosign, backed by Emergence Capital, Echosign was bought by Adobe and is Adobe Sign as we know it today.

In Today’s Episode with Jason Lemkin You Will Learn:

1.) Origins into Venture:

  • How Jason made his way into the world of venture having sold EchoSign?
  • What were some of Jason's biggest lessons from his first 4 investments being unicorns?

2.) The Importance of Ownership & Multi-Stage Funds

  • How does Jason assess the importance of ownership today?
  • If companies can be $20BN, does ownership really matter?
  • How does Jason advise founders who have offers from multi-stage funds at seed?
  • Why does taking multi-stage money at seed result in less pressure for founders?
  • Does Jason believe that signaling risk from large funds is real, when investing at seed?

3.) Building Your Sales Team

  • Does the founder have to be the one to create the sales playbook? What are the nuances?
  • Should you hire a Head of Sales or sales reps first? What should you expect from each?
  • What are the one criteria that you must look for when hiring your first sales reps?
  • What are the signals that a sales rep or leader is a 10x hire?
  • What works when hiring sales reps, 80% of the time?

4.) Boards and VC Value Add:

  • Why has Jason changed his mind when it comes to boards? Why are some inefficient and some very efficient?
  • How do the best founders manage their board? How do they bring in their exec team?
  • What is the right documentation to prepare for board meetings? Why does Jason prefer slide decks over Notion and Coda?
  • How can leaders use board meetings to direct and goal set with functional leads?

Item’s Mentioned In Today’s Episode with Jason Lemkin

Jason’s Most Recent Investment: Owner

May 4, 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.
  • Why does Chris believe we have bred a generation of asshole kids?
  • What is the right way to negotiate with children? How has that impacted how he manages his team?

Anne Wojcicki is the Founder & CEO @ 23andMe, offering DNA testing with the most comprehensive ancestry breakdown, personalized health insights, and more.

  • How did having kids change Anne's approach to time allocation and risk?

Harley Finkelstein is the President of Shopify. Over the last 12 years, Harley has partnered with Tobi to the tune of building Shopify’s revenue to over $4.6BN in 2021 and the team to over 10,000 employees. 

  • Does Harley believe he has always been a good father?
  • What changes has Harley made to be more present and there for his children?
  • Why does Harley advise couples therapy as early in a relationship as possible?

Deena Shakir is a Partner at Lux Capital, one of the leading firms investing in emerging science and technology ventures at the outermost edges of what is possible.

  • What specific negotiation tactics from parenting can be applied to business?
  • How can a parent show their children they listen, they understand and are there for them?
  • Why does Deena believe children make you more productive and more efficient?

Eric Liaw is a General Partner @ IVP, one of the leading later-stage venture capital and growth equity firms of the last decade with $8.7 billion of committed capital and a 40-year IRR of 43.1%.

  • What have been the biggest challenges for Eric of managing family and work?
  • What have been some of Eric's biggest lessons in terms of how he communicates about his work to his family?

Scott Dietzen is Vice Chairman of the Board of Pure Storage and served as the Company’s CEO from 2010 to 2017. Under his leadership, Pure grew to thousands of employees and
completed an IPO in 2015.

  • What can parents learn from nature programs?
  • What core elements of parenting are directly transferrable to management?
May 2, 2022

Harley Miller is the Founder and Managing Partner @ Left Lane Capital, one of the fastest-growing growth equity firms of the last five years. Just yesterday, Left Lane announced the closing of their new fund taking their AUM to over $2BN with an early portfolio including M1 Finance, Masterworks, Choco, GoStudent, to name a few. Prior to founding Left Lane, Harley spent over 9 years at Insight Partners investing in the likes of DeliveryHero, HelloFresh, N26, Calm, Udemy and many more breakout companies.

In Today’s Episode with Harley Miller You Will Learn:

1.) Origins into Venture:

  • How Harley made his way into the world of venture with his first role at Insight?
  • What were Harley's biggest lessons and takeaways from 10 years at Insight?

2.) Left Lane: Fundraising

  • What are harley's biggest takeaways on fundraising from speaking to 2,500 LPs for Left Lane I?
  • With that experience in mind, what advice does Harley give to other first time fund managers on what it takes to raise successfully?
  • How did the Left Lane pitch to LPs change over time? What worked? What did not work?
  • With the benefit of hindsight, what fundraising elements would Harley have done differently?

3.) Left Lane: Firm Building

  • What are the hardest elements of building a firm today?
  • How did Harley navigate the transition from investor to fund manager? What was challenging?
  • What is Harley's biggest advice to young people in venture looking to scale their career fast?
  • What are 1-2 core inputs aspiring VCs should focus on as they build their career?

4.) Left Lane: Investing and Consumer

  • How does Harley approach portfolio construction with the new fund?
  • How does Harley think through outcome scenario planning and ownership requirements with the new fund?
  • How does Harley think traditional growth equity models can be applied to consumer investing?
  • What will Left Lane be in 20 years? What firm does Harley want to build?

Item’s Mentioned In Today’s Episode with Harley Miller

Harley’s Most Recent Investment: Masterworks

Apr 29, 2022

Noah Glass is the Founder and CEO @ Olo, the interface between restaurants and the on-demand world powering millions of orders per day. Olo is an incredible tale of capital efficiency, at IPO the company had a net burn of just $6M with $122M in ARR. Noah raised from some of the best in the business with names such as David Frankel @ Founder Collective, Danny Meyer, Scott Shleifer @ Tiger Global, all on the cap table. Prior to founding Olo, Noah was International Expansion Manager for Endeavour Global, launching the first African Endeavour affiliate. If that was not enough, Noah is also on the board of Portillo's, Share our Strength and the Culinary Institute for America.

In Today’s Episode with Noah Glass You Will Learn:

1.) The Founding of Olo:

  • What was the founding a-ha moment for Noah with Olo?
  • What did David Frankel do that compelled Noah, now was the time to start Olo?
  • What have been some of Noah's biggest lessons from working with David Frankel?

2.) Capital Efficiency: Scaling to $122M ARR with $6M Net Burn

  • Why did Noah and the team not raise more money in the early Olo days?
  • How does Noah advise early founders who are concerned if they do not raise, their competition will?
  • What are 2-3 of the core levers that allow Olo to be so efficient? What can others learn from them?
  • What would Noah have done differently fundraise wise, with the benefit of hindsight?

3.) Decision Making: The Secret

  • What does Noah mean when he says; "capital allocation and attention allocation are intertwined"?
  • How has Noah changed and evolved his decision-making as a leader?
  • How does Noah use a CEO coach? What do they discuss? How often? What works? What does not?
  • What decision did Noah make that proved to be the wrong one? How did he come back from it?

4.) Noah Glass: The Father and Husband

  • How does Noah do so much as CEO and also not lose an inch on being an amazing father and husband?
  • What does Noah believe is the secret to a truly successful marriage, while also being public markets CEO?
  • How has Noah changed as a father and husband over the years? What has worked? What has not worked?

Item’s Mentioned In Today’s Episode with Noah Glass

Noah’s Favourite Book: Setting the Table by Danny Meyer

Apr 27, 2022

Mitch Tarica is Head of North America Sales at Zoom Video Communications. Before joining Zoom, Mitch spent over 5 years at RingCentral including as Senior VP of Worldwide Sales and Customer Success. Finally, before RingCentral, Mitch was at Oracle for over 7 years in numerous different sales roles.

In Today’s Episode with Mitch Tarica You Will Learn:

1.) Entry into Sales:

  • How did Mitch make his way into sales with one of the first SaaS companies in the world?
  • What were his early lessons on what truly great sales entails?
  • What elements does Mitch fear we have lost in the art of sales over time?

2.) The Playbook:

  • Should the founder be the one to create the sales playbook?
  • What are the signs that the founder has a repeatable and scalable playbook?
  • When is the right time to make the first sales hire? Should it be a Head of Sales or Sales Rep?
  • How does the first hire depend on whether you are PLG or enterprise sales led?

3.) The Hiring Process:

  • How does Mitch structure the hiring process? Step by step, what does he want to achieve?
  • What questions does Mitch ask in the first interview, always?
  • What are the 3 traits that Mitch believes all great sales hires have? How does he test for them?
  • How do Zoom use practical sales tests to determine the ability of a potential sales hire?
  • How does Mitch see many founders make mistakes in the sales hiring process?

4.) Sales Onboarding:

  • What are the crucial steps to do sales onboarding right?
  • How should leaders structure the first 30,60 and 90 days for their new reps?
  • What are some early red flags that leaders should watch for with new reps?
  • What more can leaders do to make sure their reps are as successful as possible in the early days?

Apr 25, 2022

Deena Shakir is a Partner at Lux Capital, one of the leading firms investing in emerging science and technology ventures at the outermost edges of what is possible. Deena has led a number of investments including in Maven Clinic, Mos, Ramp, Alife and SteadyMD to name a few. Before joining Lux, Deena was a Partner at GV and previously led product partnerships at Google for early-stage products in healthcare, AI/ML and search at Google. Before tech and venture, Deena was an aspiring anthropologist, journalist, diplomat, aid worker and was a Presidential Management Fellow at the U.S. Department of State under Secretary Clinton. There Deena helped launch President Obama’s first Global Entrepreneurship Summit in 2010.

In Today’s Episode with Deena Shakir You Will Learn:

1.) Origins into Venture:

  • How Deena made her way from journalism and the world of politics to rockstar healthcare investor?
  • What were Deena's biggest takeaways from seeing her parents build a new life in the US?

2.) Competition in Venture:

  • Why should founders not take multi-stage fund money at seed?
  • What problems does it cause? How do VCs try and justify it? What red flags should founders look for?
  • How does Deena advise her companies when it comes to pre-emptive rounds? When should they take them? When should they not take them?

3.) Deena Shakir: The Person

  • How has becoming a parent changed Deena's operating mentality?
  • Why does Deena believe she has never been better as an investor post becoming a mother?
  • Why does Deena feel so many questions around parenting are wrong? In what ways would she like those questions of female operators and investors to change?

4.) Diversity and Inclusion: We Should Be Optimistic

  • Why is Deena optimistic about the future of diversity and inclusion in tech and venture?
  • What drives her optimism? What remains a cause for concern for Deena on this topic?
  • What more can both companies and venture funds do to improve the landscape?

Item’s Mentioned In Today’s Episode with Deena Shakir

Deena's Favourite Book: The Power Law: Venture Capital and the Art of Disruption

Deena's Most Recent Investment: Mos: Banking for Students

Apr 22, 2022

Bill Cillufo is Partner and Head of International Investments at QED, one of the leading fintech venture firms today with a portfolio including Nubank, Kavak, Klarna, Quinto Andar and Bitso to name a few. As for Bill, he has led investments in Nubank, Loft, Wagestream and Creditas among others. Prior to joining QED, he spent nearly 20 years at Capital One, spanning several roles and leading several businesses. During Bill’s last 3 years at Capital One, he led its Co-Brand and Private Label credit card business, building the business nearly from scratch to one of the top few players in the US market.

In Today’s Episode with Bill Cillufo You Will Learn:

1.) Origins into Venture:

  • How Bill made his way from 20 years at Capital One to becoming a Partner @ QED?
  • How did Capital One inform his mindset around unit economics?
  • Having seen booms and busts firsthand with Capital One, how did that impact his investing mindset today?

2.) The Landscape: What is Happening?

  • Where does Bill believe the biggest crunch in funding markets is today?
  • Does Bill believe this will trickle down to the early stage?
  • How does Bill advise his portfolio companies on runway and burn given the environment?
  • What does Bill believe that many have not seen that is coming?

3.) Bill Cillufo: The Investor

  • How does Bill analyse his own relationship to price and price sensitivity?
  • How has Bill changed as an investor over the last 5 years? What caused the changes?
  • How does Bill reflect on reserves management given the new landscape we are in?

4.) QED: The Expansion

  • Does Bill believe that expanding geographically has become easier with time?
  • What has become harder about expanding into new geographies?
  • How important does Bill believe partnering with local firms is when VCs enter new territories?

Item’s Mentioned In Today’s Episode with Bill Cillufo

Bill’s Favourite Book: Tom Clancy: The Hunt for Red October

Bill’s Most Recent Investment: Refyne

Apr 20, 2022

Aparna Chennapragada is Chief Product Officer @ Robinhood, the company revolutionizing consumer finance with commission-free investing, and tools to help shape your financial future. As for Aparna, prior to Robinhood, she spent an incredible 12 years at Google, most recently as VP and GM for Consumer Shopping and also as the lead AR and Visual Search products. Aparna is also an active angel investor with a portfolio including Khatabook, Statsig and On Deck to name a few. If that was not enough, Aparna is also a board member at Capital One.

In Today’s Episode with Aparna Chennapragada You Will Learn:

1.) Origins in Product:

  • How Aparna made her way into the world of product and product management?
  • What were Aparna's biggest takeaways from her 12 years at Google?
  • What does product management mean to Arpana today?

2.) Customer Discovery: 101

  • What are the 3 different stages of product management?
  • What does great customer discovery look like?
  • What are the best questions to ask? How should one dig deeper?
  • Where do so many make mistakes in customer discovery?
  • What should product people take from the answers? What should they disregard?

3.) The Hiring Process:

  • How should founders breakdown the process of hiring for their first in product?
  • What does the interview process look like? How should founders structure it?
  • What core questions should teams ask of prospective candidates?
  • What are red flags when interviewing potential product hires?
  • What literal tests and case studies can founders do to test the quality of candidates?

4.) The Onboarding Process:

  • How should founders structure the onboarding process for new product hires?
  • What can founders do to make PMs successful in their first 30 days?
  • Where do many product hires make the biggest mistakes in the first 30 days?
  • What can product hires do to build trust with their new team?

Items Mentioned in Today's Episode with Aparna Chennapragada

Aparna's Fave Resource: Shishir's Executive Onboarding

Apr 15, 2022

Henrique Dubugras is the Founder and CEO @ Brex, the company re-imagining financial systems so every growing company can realize its full potential. To date, Henrique has raised over $1.1BN for Brex from some of the best including Ribbit, Greenoaks, DST, IVP, Caffeinated Capital and Elad Gil to name a few. Henrique is also a board member at Mercado Libre. Prior to co-founding Brex, Henrique co-founded, there he scaled the company to $15BN in GMV and over 100 people before selling the company in 2016.

In Today’s Episode with Henrique Dubugras You Will Learn:

1.) The Founding of Brex:

  • What was the founding a-ha moment for Henrique and Pedro with Brex?
  • What advice did Evan Spiegel give Henrique when it comes to being a great CEO?

2.) Hiring: The Trials and Tribulations

  • What have been Henrique's biggest hiring mistakes?
  • How do founders know when they are ready to bring in the seasoned exec vs the younger jack of all trades candidate?
  • What have been Henrique's biggest lessons in what it takes to hire true A* talent?
  • Where does Henrique see other founders make big hiring mistakes?

3.) Product Expansion and Marketing:

  • How does Henrique assess when is the right time to release a second product?
  • What have been Henrique's biggest mistakes and lessons when it comes to product marketing?
  • How can one retain the simplicity of product messaging with scaling the product?
  • Brex expanded the product too far, too fast. How did they walk it back so successfully?

4.) Henrique: The Leader

  • How does Henrique approach his own relationship to money today? How has it changed over time?
  • What luxury expenditure has Henrique made over the last 12 months that he feels is worth it?
  • How does Henrique think about ego management? What does he do to keep his in check?

Item’s Mentioned In Today’s Episode with Henrique Dubugras

Henrique’s Favourite Book: The Innovator's Solution: Creating and Sustaining Successful Growth

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