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

Grant LaFontaine is the Founder & CEO @ Whatnot, the fastest-growing marketplace in the US, empowering people to make a living off their passion. To date, Grant has raised over $225M for Whatnot from the likes of CapitalG, a16z, YC, Scribble Ventures and Wonder Ventures to name a few. Prior to Whatnot, Grant was a PM @ Facebook working on the Oculus App Store and before that was the founder of Kit.com, ultimately acquired by Patreon.

1.) The Founding of Whatnot:

• How did Grant make his way into the world of tech and startups?
• What were some of his biggest lessons from Facebook? How did that impact how he has built Whatnot?

2.) Impossible To Hire Product Managers:

• Why does Grant believe it is impossible to hire product managers today?
• How does this impact the decision-making powers of engineers?
• How does Grant test for this product knowledge in all engineers he adds to the team?
• What are clear signals of 10x engineers in hiring processes?

3.) A/B Testing and Risk Mindset:

• Why does Grant not believe in the effectiveness of A/B testing? Why does it not work?
• Why does Grant believe one of the biggest reasons for startups failing is they do not take enough risk?
• How does Grant try to ensure that his team takes as much risk as possible with everything that they do?
• How does mindset to risk change with scale of company and with leadership?

4.) AMA:

• Why does Grant disagree with founders angel investing?
• What are the biggest challenges Whatnot has faced in scaling?
• CEO coach? Who? When? What is the biggest lesson?
• What is the single driving metric of Whatnot? How does Grant advise founders to determine their North Star metric?

Grant's Favourite Book: Foundation: 1/3 (Foundation Trilogy)

Luciana Lixandru is a Partner @ Sequoia, one of the world's most renowned and successful venture firms with Sequoia-backed companies accounting for more than 20% of NASDAQ's total value. As for Luciana, at Sequoia she has led investments in the likes of PennyLane, Xentral, Veed and Ledgy to name a few. Prior to joining Sequoia in 2020, Luciana was a Partner @ Accel where she made investments in Hopin, Miro, UiPath, Tessian and Deliveroo. As a result of such investing success, Luciana was #2 on the Midas List in 2021.

1.) Origins:

• How did Luciana make her way from a small town in Romania to being Partner @ Sequoia?
• What were the 1-2 crucible moments in her life that changed the course of her life?

2.) Luciana: The Investor

• How has Luciana's investing style changed and developed over the years?
• How does Luciana reflect on her own relationship to price? What misses caused these changes?
• Hopin, Miro, Deliveroo, UiPath, how did having such winners so early impact Luciana's investing mindset?
• What would Luciana say is her biggest insecurity today? What drives this?

3.) Sequoia: The Team

• What are Luciana's biggest takeaways from working with Doug Leone, Alfren Lin, Roelof Botha and Pat Grady?
• What does the decision-making process look like for new deals within Sequoia?
• How does the Sequoia partnership create an environment of safety where everyone can discuss and debate freely?
• How does Luciana approach training and mentorship? What works and what does not?

4.) Sequoia in Europe + Sequoia's Arc:

• What is Arc? Why was now the right time for Sequoia to do it?
• What is the structure for the program?
• How many startups are part of it? Who is able to apply?
• How much capital do the startups receive? What else do they receive in mentoring etc?
• In 5 years time, what would success look like for Luciana with Arc?

Luciana's Favourite Book: The Spy and the Traitor: The Greatest Espionage Story of the Cold War

Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. This has scaled to thousands upon thousands of readers and is one of the most popular newsletters on Substack. Lenny is also an extremely active angel investor with a portfolio including Figma, Sorare, Clubhouse, Vanta, WhatNot and many more incredible companies. If that was not enough, Lenny also has the best course on product management, check it out here.

1.) Origins in Product:

• How did Lenny make his way iunto the world of product management at Airbnb?
• What were some of his biggest takeaways from his time at Airbnb on product?
• What mistakes did he make on product at Airbnb? How did it impact his product thinking?

2.) Product Management: 101

• How does Lenny define product management today? How is the role of PM changing?
• When is the right time to hire your first PM as a startup?
• What is the difference between Head of Product and CPO? When do you hire each?
• What are the biggest mistakes founders make when hiring their first product hires?

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?

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 Lenny Rachitsky

Lenny's Fave Book: The Mom Test

David Friedberg is Founder and CEO of The Production Board (TPB), a holding company established to solve the most fundamental problems that affect our planet, by reimagining global systems of production. Prior to founding The Production Board, David founded The Climate Corporation, a 10-year journey that culminated in their $930M acquisition by Monsanto. If that was not enough, David is the Founder and Chairman at Metromile and also sits on the board of Soylent, Clara Foods, Tillable, Cana Technologies and more.

1.) Origins:

• How David made his way into the world of startups and technology from academia and physics?
• What were David's biggest takeaways from scaling The Climate Corp to $930M exit to Monsanto?
• How did the exit put pressure on David for all future companies he builds? How does he manage that?

2.) The Macro: Venture + The Economy

• How does David foresee the impending rate hikes? What impact will this have on venture and the economy?
• What segment of the market will be first to be hit? Why is growth investing last to be hit? How does early stage play out in this very new environment?
• How will we see the velocity of capital deployment change in this new period? What does David believe are some of the crucial flaws of the venture model?
• How does David reflect on his own price sensitivity? What lessons has he learned from deals he has done or missed that have changed his perspective?

3.) David Frankel: The Business Builder

• What is David's rubrik for business value creation? How has this changed with time?
• How mentally plastic does one have to be around the time it takes to see margins, unit economics etc change from negative to positive?
• How does David and the team approach building new companies at TPB? Where do they find the founding teams? How do they incentivise them?
• How does TPB approach continuous funding for the companies they create? What milestones need to be hit? How do they assess them?
• How does David approach liquidity with regards to exits for the companies they create? Why does their holding company structure mean they have different incentives to VCs?

4.) David Friedberg: Father and Husband

• How does David reflect on his own relationship to money today? How has it changed over time?
• What have been David's biggest realisations on what provides him true happiness?
• How did having children change his operating mentality? What does being a great father mean to David?

David's Favourite Book: Zen Mind, Beginner's Mind

Sid Sijbrandij is the Co-founder & CEO @ GitLab. GitLab's single application helps organizations deliver software faster and more efficiently while strengthening their security and compliance. Prior to their IPO last year, Sid raised funding from some of the best including ICONIQ, GV, Tiger, Coatue and D1 to name a few. Under his leadership, the company has grown to over 1,500 employees and over 30 million registered users. If that was not enough, Sid is also an active angel and sits on the board of Meltano, a spinout of Gitlab that allows you to manage all the data tools in your stack.

1.) The Founding of Gitlab:

• How did Sid make his way into the world of tech and startups?
• What was it about Gitlab as a project that excited Sid so much from Day 1?
• How did Sid convince his co-founder to turn Gitlab from a project into a company?

2.) The Future of Work:

• Why does Sid believe it is a fallacy that everyone will go back to the office?
• What are the 1-2 most important things for companies to do when moving to a remote work environment? Where does Sid see many make mistakes?
• What have Gitlab done to create a remote working environment so successfully? What have they tried that has not worked?
• What stage of company building does remote work best for? When is it most challenging?

3.) Sid: The Leader

• How has Sid changed and evolved as a leader over the Gitlab journey?
• How does Sid look to get as much feedback as possible on his leadership?
• How does Sid create an environment of safety where everyone feels they can provide feedback?
• How does Sid work with his CEO coach? Should every CEO have one? What should one look for in them? How do you know when you need to change your CEO coach?

4.) Sid: The Board Member:

• What have been Sid's biggest lessons on what makes successful board management?
• In prep for the meeting, what materials does Sid provide? When does he send them? Does he present to the board? What mistakes do founders make in boards?
• From being on the other side as a board member, what does Sid believe the best members do?
• What would Sid most like to change about board meetings today?

Sid's Favourite Book: High Output Management

Jeanne DeWitt Grosser is Head of Americas Revenue & Growth @ Stripe. In this role, Jeanne is responsible for all sales functions across the region including Sales Development, AEs, Solutions Architects, and many more. Jeanne also continues to spearhead Stripe's Enterprise strategy. Prior to this role, Jeanne was Stripe's Head of North America Sales where she built out Stripe's Acquisition Sales teams. Pre-Stripe, Jeanne was CRO @ Dialpad and also spent many years at Google in numerous different roles including most recently as Director of GSuite SMB & Mid-Market Sales, North America and LATAM.

1.) Entry into Sales:

• How did Jeanne make her way into her first sales job in tech?
• What did Jeanne learn from her many years at Google about how sales should interact with engineering?
• In hindsight, what would Jeanne have done differently/improved from her time with Dialpad?
• How did the role with Stripe come about?

2.) The Playbook:

• Does the founder need to be the one to create the sales playbook?
• When is the right time to bring in the first sales hire? Should they be a sales leader or rep?
• How does both the playbook and the type of sales hire change when hiring for a product-led-growth motion vs a traditional enterprise motion?
• What are the single biggest mistakes founders make when hiring their first in sales?

3.) The Hiring Process:

• How should founders structure the hiring process for their first sales hires?
• What did Dialpad do in the sales hiring process that worked well? How has Jeanne taken that to her hiring process at Stripe?
• What should be achieved or learned in each consecutive interview?
• How can founders use sales case studies most effectively? How can founders know if sales candidates truly have a strong grasp of the product?
• What are early signs of a 10x sales hire? What are red flags to look out for in the process?

4.) Sales Onboarding:

• What does the ideal onboarding process look like for new sales hires?
• What tasks and duties should all sales hires perform in the first 60 days?
• What are early signs that a new hire is not performing to the right standard?
• How does the first few months differ for sales reps when comparing a product-led-growth company to an enterprise company?
• What should sales leaders do to ensure that new hires engage with product and customer success efficiently?

Harley Finkelstein is the President of Shopify, the platform modern commerce is built on. 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. On the side, Harley is an Advisor to Felicis Ventures and in the past has held board seats at CBC, Omers Ventures and The C100. If that was not enough, you can see Harley on a screen near you as one of the "Dragons" on CBC's Next Gen Den.

1.) The Founding Story:

• What was Harley's first entrepreneurial endeavour?
• How did seeing his family lose everything impact Harley's mindset and ambition?
• How did Harley first meet Tobi @ Shopify? How did the Shopify journey begin?

2.) Leadership Lessons:

• How has Harley changed as a leader over the 13 years with Shopify?
• How does Harley embrace vulnerability and authenticity in his communication with the team?
• What is Harley most insecure about when he looks at leadership today?
• What have been some of the biggest lessons Harley has learned from his board on what great leadership is?

3.) The Art of Marriage:

• What does Harley believe makes the most successful marriage?
• Why have Harley and his wife been seeing a marriage therapist from the early days?
• What is the biggest mistake people make when communicating with partners?
• How has Harley changed as a husband over the years?

4.) The Joy of Fatherhood:

• Does Harley always believe he has been a good father?
• What was his realisation moment that he was not being the father he wanted to be?
• What core elements of his behaviour did he change? How did that impact his relationship with his kids?
• How does Harley ensure he performs at the highest level while also being there and being present for his family?

Harley's Favourite Book: The Book of Ichigo Ichie: The Art of Making the Most of Every Moment, the Japanese Way

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. Dietzen is a four-time successful entrepreneur with WebLogic, Zimbra, and Transarc. Before Pure, he was President and CTO of Zimbra (now part of VMware), but originally acquired by Yahoo!, where Dietzen served as interim SVP of Communications and Communities. Prior to Zimbra, Dietzen was CTO of BEA Systems, where he helped craft the technology and business strategy for WebLogic that drove BEA from $61m in annual revenues prior to the WebLogic acquisition to over $1B.

1.) The Journey to Pure Storage CEO:

• How did Scott make his way into the world of tech and startups?
• What was the hardest element of making the transition from CTO to CEO?
• What advice would Scott give to more technical leaders looking to make the move to CEO? Where do so many make mistakes?

2.) How To Build Trust in a Team:

• What are the most important ways that leaders can build trust with their teams?
• How can leaders be honest and share the hard truths without damaging role?
• What is the right tone to communicate both the big wins and big losses?
• Why does Scott always believe the losses teach more? How does Scott approach post-mortems?

3.) The Biggest Mistakes Founders Make:

• What are the single biggest hiring mistakes that founders make?
• What are the single biggest firing mistakes executives make?
• Why should founders sometimes say no to customers?
• How should founders approach investor selection and valuation for rounds?

4.) How to Optimise a Board:

• What specifically can founders do to optimise their board?
• What are the biggest errors founders make when communicating with their board?
• What is the value per word framework? How does it tell which board member is the best?

Scott's Favourite Book: The 22 Immutable Laws Of Marketing

Sahil Bloom is the Founding Partner @ SRB Ventures, a $10M fund that leverages the 500K followers Sahil has amassed to invest at the intersection of venture and media. Previously, Sahil spent 7 years at a large investment fund managing >$3.5 billion in capital and serves on the board of 4 companies. He has also been an active angel investor in over 30 companies.

1.) How Sahil made his way from a career in traditional finance to building a media company and leveraging that to raise the latest SRB fund? How does Sahil advise others is the best way to "find their zone of genius"?

2.) How To Build a Media Engine:

• What have been some of Sahil's biggest lessons on what works on Twiter and what does not work?
• What is the golden rule for Twitter?
• How does Sahil plan and come up with ideas for his Twitter threads? What tools and software does he use? How long does each thread take?

3.) The End of the Road for Traditional Venture:

• Why does Sahil think traditional venture is dying?
• What newcomers will take the place of the existing incumbents?
• Why does he think they are weak? What do new players provide that they do not?
• Which existing players will remain and be strong? Which will fade out?
• Does Sahil believe that VCs really provide any value?

4.) SRB Ventures:

• Why did Sahil decide to raise the new fund?
• How did he decide on size of the fund? What is the strategy? What is the portfolio construction?
• How does SRB provide media services others do not?
• How did Sahil meet Tim Cook and get him to invest in the fund?
• What is the biggest thing Sahil believes most people misunderstand about luck?

Sahil's Favourite Book: When Breath Becomes Air: Kalanithi Paul

Sahil's Most Recent Investment: Wander

Tiger Global are one of the most discussed venture firms on the planet. With a deal cadence and capital deployment speed that is unmatched, they have made their mark on the venture landscape like no other over the last 24 months. Today we are joined by leaders from Sequoia, Benchmark, Thrive Capital, General Atlantic, GGV and Aleph to discuss the rise of Tiger and how it impacts the venture ecosystem.

1.) Doug Leone: Sequoia Capital

• Why we need to change the words when use in venture? Why we need to get rid of "the game"?
• How does the rise of Tiger compare to the rise of prior entrants with the same approach?
• Why does Doug believe that the craft of venture will persist despite these new entrants?

2.) Bill Gurley: Benchmark Capital

• How does Bill analyse the change in late stage venture today?
• What are the main drivers of the increased competition in late stage venture?
• Why does Bill get concerned not by Tiger but how others respond to Tiger's model?
• How does Bill analyse the entry of hedge funds and PE funds into traditional venture models?

3.) Michael Eisenberg: Aleph

• How does Michael think about the "weaponisation of capital"?
• What are the significant benefits for a fund of having more capital than their competitors?
• How does this capital advantage change in boom and bust times?

4.) Anton Levy: General Atlantic

• Why does Anton believe that funds are leveraging their assets more efficiently than ever?
• How does Anton approach the mindset of AUM scaling without lowering returns?
• Why does Anton never want to compete on price?
• How does GA think about competing in a world of Tiger and hedge funds investing in tech?

5.) Hans Tung: GGV

• Why did Hans always believe the model to look at moving forward was Tiger?
• Why does Tiger's business model allow them structural and financial advantages over their competitors?
• What does Hans make of the data network effects of Tiger with their strategy?

6.) Kareem Zaki: Thrive Capital

• Why does Kareem think Tiger's approach makes absolute sense?
• Why does Kareem believe so many in venture like to try and discredit the Tiger model?
• How does Tiger's approach differ to Thrive's?