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

Bill Gurley is a General Partner @ Benchmark Capital, Bill, is widely recognized as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix, and Zillow.

Doug Leone is the Global Managing Partner @ Sequoia Capital, one of the world's most renowned and successful venture firms with a portfolio including the likes of Google, Airbnb, Whatsapp, Stripe, Zoom and many more.

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.

Arthur Patterson and Jim Swartz founded Accel in 1983. Under their leadership, they have built Accel into one of the most prominent venture firms of the last 4 decades.

Michael Eisenberg is a Co-Founder and Equal Partner @ Aleph, with a portfolio including the likes of Lemonade, Melio and HoneyBook, they are one of the leading early-stage firms of the last decade.

Sonali De Rycker is a Partner @ Accel, one of the leading firms of the last 3 decades with a portfolio that includes the likes of UiPath, Miro, Spotify and many more incredible companies.

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 many more.

1.) How does the current environment compare to prior busts?

2.) How will the changing interest rates impact the startup funding climate moving forward?

3.) Why is the rate of inflation the only true metric which reveals the ultimate fate of the economy?

4.) What are the world's leading investors telling their founders?

5.) How are the best investors in the world thinking through reserves management?

Sonali De Rycker is a Partner @ Accel, one of the leading firms of the last 3 decades with a portfolio that includes the likes of UiPath, Miro, Spotify, and many more incredible companies. As for Sonali, Sonali led Accel's investments in Avito (acquired by Naspers), Spotify (NYSE: SPOT), Primer, Monzo, Letgo (acquired by Naspers), Kry/Livi, Soldo, Hopin, and Sennder. Prior to Accel, Sonali was with Atlas Venture (now Accomplice). She also previously served on the board of Match.com (NASDAQ:MTCH).

1.) From Small Town in India To Leading Venture Capitalist:

• How Sonali made her way from a small town in India to becoming one of the most prominent VCs of the last decade?
• What were some of Sonali's biggest lessons from seeing the booms and busts of 2000 and 2008? What climate does the crash today resemble more? Why so?
• How does Sonali advise younger investors who have not lived through a downturn? What should their investor psychology be right now?

2.) Firm Building: Accel:

• What are the most challenging and non-obvious elements of building a firm today?
• What have been some of the biggest mistakes Accel has made when adding to the team?
• What qualities do Sonali and Accel specifically look for when interviewing candidates to join the team? What specific questions tease out whether the candidate has these traits?
• What specific structures does Accel have in place to encourage the team to work together as one cohesive unit? How do they use bonuses as a team incentive?

3.) Sonali: The Investor:

• How has Sonali's investing style changed over the years? What moments caused these changes to happen?
• What are some of the biggest mistakes Sonali has made in her investing career? What did she learn from them?
• On the flip side, from winners such as Spotify and Supercell, what did Sonali learn from her biggest winners?
• Why does Sonali believe that market sizing and outcome scenario planning is useless and will lead you to make the wrong decision?

4.) Decision-Making and Risk:

• What does Sonali mean when she speaks of Type 1 and Type 2 decisions? How should one's decision-making process change according to which type of decision it is?
• What are the two biggest risks startups are facing today? Does Sonali believe that seed-stage companies will take money from crossover funds?
• What does Sonali do when she loses faith in the founder? How does she communicate that to them in the right way? What have been some of her biggest lessons here?
• What have been some of Sonali's biggest lessons when it comes to reserves management? How does Sonali determine when to double down vs reserve cash?

Sonali's Favourite Book: A Fine Balance

Sonali's Most Recent Investment: BeReal

Henri Pierre-Jacques is Managing Partner of Harlem Capital, on a mission to change the face of entrepreneurship by investing in 1,000 diverse founders over the next 20 years. From a kitchen table with his Co-Founder, Jarrid, Henri has scaled Harlem in just a few years to their latest fund last year of $134M, well over-subscribed from their $100M target. Prior to Harlem, Henri was in Private Equity at ICV Partners, and before PE was an Investment Banker at Bank of America Merrill Lynch.

1.) From Kitchen Table to $134M Fund:

• How did Henri make his way into venture having had the idea for Harlem at the kitchen table with his best friend?
• How did Henri use his angel investing strategically to position him to raise Fund I?
• How did Henri's mindset change when making the transition from angel to VC?

2.) The First Fundraise: Harlem I

• How long did it take to raise the first fund? How many meetings did they have?
• What were the most common reasons LPs said no for the first fund?
• What were their biggest lessons around what potential LPs did and did not like?
• How does Henri advise new managers when it comes to meeting new LPs?
• How does Henri use past deal memos to serve as discussion material with LPs?

3.) Building the Firm: The Strategy:

• What was the portfolio construction for the first fund?
• How does Henri separate the world of funds into 3 distinct groups?
• How did they approach reserves management with the first funds? What are some of Henri's biggest lessons when it comes to effective reserves management?
• How does Henri assess his own relationship to price and ownership? How does that change with fund size?
• What are some very important nuances that Henri does not believe many managers think about?

4.) It Is Time For Change:

• Specifically, what are Harlem street doing to ensure the next generation of investors is much more diverse? How do they leverage their intern program to achieve this?
• What would Henri like to see change in the world of LPs when it comes to allocating to more diverse managers?
• What legacy does Henri want to leave with Harlem? What will be a success for Henri?

Henri's Most Recent Investment: Mueshi

Zhenya Loginov is the CRO @ Miro, the leading visual collaboration platform that helps bring teams together and meaningfully improves the way people work. At Miro, I run the go-to-market team of 700+ people across 11 global offices. Prior to Miro, Zhenya was the COO @ Segment where he built and ran the global go-to-market team of 200+ people, expanded the product-market fit into the Enterprise and grew revenue 6x, leading to their acquisition by Twilio for $3.2Bn. Finally, before Segment, Zhenya led a 100-person team at Dropbox across numerous different functional areas.

1.) Entry into Sales as an Outsider:

• How Zhenya made his way into sales as an outsider and came to be one of the most powerful revenue leaders today with Miro?
• What are 1-2 of the biggest takeaways for Zhenya from his time at Segment and Dropbox? How did they impact his mindset today?
• Why did Dropbox not win the enterprise when they had the chance? What mistakes did they make?

2.) The Sales Playbook: What, Why and How:

• What does "the sales playbook mean to Zhenya?
• Does the founder need to be the one to create the sales playbook?
• What are the signs that the founders needs to bring in their first sales hire?
• Should this sales hire be a sales leader or more junior sales rep?
• Is is possible to run a PLG and enterprise sales motion at the same time in the early days of the company?
• What do many founders misunderstand when contemplating adopting an enterprise sales strategy?

3.) Hiring the Team:

• How does Zhenya structure the interview process for new sales hires?
• Zhenya spends 5 hours with each candidate, what does he look to get out of each meeting?
• How does Zhenya break down the criteria for what he wants to see? What are some examples of this?
• How does Zhenya test to determine if the candidate has these criteria? What questions does he find to be most revealing? Why does Zhenya find case studies to not be useful?
• How does Zhenya use interview panels to ensure he makes the right hiring decision? Who is on the panel? At what stage do they meet the candidate? How does Zhenya like to use the panel?

4.) Laying the Groundwork: The Onboarding Process:

• What is the right way to structure the onboarding process for all new sales hires?
• What are some early signs that a new sales hire is not working?
• What can sales leaders do to ensure new reps get "early wins" on the board?
• What can leadership do to ensure the sales team has good cross-functional communication across the org? What works? What does not work?
• What are some of the biggest challenges of running a remote sales team?

Gary Vaynerchuk is a serial entrepreneur and serves as the Chairman of VaynerX, the CEO of VaynerMedia and the Creator & CEO of VeeFriends. Now Gary is a content machine and documents his life as a CEO daily through his social media channels which have more than 34 million followers and garnishes over 272 million monthly impressions/views across all platforms. He is also a five-time New York Times Best-Selling Author and is a prolific angel investor with early investments in companies such as Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase and Uber. If this was not enough, Gary serves on the board of GymShark, MikMak, Bojangles Restaurants, and Pencils of Promise.

1.) From Wine Library to One of The Great Angels in Tech:

• How did Gary make the transition from scaling the wine library to $60M in revenue to angel investing in Twitter, Facebook and Tumblr?
• To what extent does Gary think luck plays a role in one's success today?
• What are Gary's biggest lessons from having FB, Twitter and Tumblr as his first investments? How has his style of angel investing changed over time?

2.) Hard Lessons Learned and Insecurity:

• What is the most painful lesson Gary has learned that he is also pleased to have learned?
• How did Gary's relationship with his father impact how he engages with his children as a father today?
• What are Gary's biggest insecurities today? How does he try and combat them? What works?

3.) Money and Success:

• How does Gary evaluate his relationship with money today? How has it changed over time?
• Why does Gary believe that most people think too short-term? What can one do to inspire a more long-term mindset to building?
• Does Gary believe that everything has a price? What is the one thing for Gary that does not have a price?

4.) Resource and Time Allocation:

• How does Gary determine the projects to do vs not to do?
• How does Gary know when to quit a new project? How does Gary advise founders on when something is not working and knowing when to quit?
• What are some of the biggest mistakes Gary sees founders make when it comes to resource allocation in the early days?

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.

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?

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.

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?

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

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 OnStartups.com -- 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.

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?

The Hubspot Culture Code

Dharmesh's Favourite Book: Les Miserables

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.

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?

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.

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?