20VC: Robinhood Founder Vlad Tenev on The Single Most Important Thing Leadership is Responsible For, How To Manage Fear and Self-Doubt as a Leader & The Future of Fintech; Bundled or Unbundled


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

Vlad Tenev is the Co-Founder & CEO @ Robinhood, the company that provides commission-free investing, plus the tools you need to put your money in motion. To date, Vlad has raised over $2.2BN with Robinhood from some of the very best in the business including Sequoia, Greenoaks, Index, DST, Ribbit, IVP, Thrive, NEA, GV and more incredible names. Before Robinhood, Vlad started two finance companies in New York City.

In Today’s Episode You Will Learn:

1.) How Vlad made his way from Bulgaria to studying Math at Stanford to founding one of the fastest-growing companies of the decade in Robinhood?

2.) How does Vlad describe his own style of leadership today? How has this changed with the scaling of the business? What phase has been the most challenging? Why does Vlad think so much about “the tempo” of the company? What can you do to ensure the highest tempo?

3.) How does Vlad think about self-doubt as a leader when recognising the sheer size of the Robinhood team today being over 1,000? How does Vlad analyse the role that fear has to play in leadership? How does Vlad manage the weight of expectation? What works? What does not?

4.) What have been Vlad’s lessons in what it takes to acquire the very best talent? Where do many founders make mistakes here? How does Vlad think about the role of mentorship with young team members? Why and how does Vlad bet so big on giving young team members responsibility?

5.) How does Vlad assess the current state of the fintech landscape today? Does Vlad believe we are entering a period of bundling or unbundling? Will we see the continued rise in the M&A activity we saw earlier this year? Why? What is likely to change in 2021?

Item’s Mentioned In Today’s Episode

Vlad’s Favourite Book: The Mars Project

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20VC: Benchmark’s Sarah Tavel on Why Chasing GMV Will Lead To The Wrong Direction, The 2 Crucial Tipping Points For Marketplace Adoption, Why UGC Plays Are Like Marketplaces & How To Determine Between Existential and Non-Existential Risk


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

Sarah Tavel is a General Partner @ Benchmark, one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many more. As for Sarah, prior to joining Benchmark, she was a General Partner at another globally renowned firm, Greylock, where she led deals in Sonder and Gixo. Pre-Greylock, Sarah was the first PM @ Pinterest where she led three acquisitions, launched Pinterest internationally, and was responsible for closing their $100m Series C financing.

20VC: Benchmark’s Sarah Tavel on Why Chasing GMV Will Lead To The Wrong Direction, The 2 Crucial Tipping Points For Marketplace Adoption, Why UGC Plays Are Like Marketplaces & How To Determine Between Existential and Non-Existential Risk

In Today’s Episode You Will Learn:

1.) How Sarah made her way from being the first PM at Pinterest to being a General Partner at one of the world’s leading venture firms, Benchmark?

2.) What does Sarah mean when she says, “the small things are not the big things”? How does Sarah determine between existential vs non-existential risk? How does this impact the type of board member Sarah is? How has Sarah seen the best board members engage? Who are they?

3.) Why does Sarah believe that in marketplaces, chasing GMV will lead you in the wrong direction? How does Sarah think about good vs great when it comes to 1.) Average order values? 2.) Repeat purchase rates. 3.) NPS? 4.) Net revenue retention? How should they change with time?

4.) In marketplaces, what is a tipping point? What are the 2 crucial tipping points to be aware of? How can marketplaces ensure demand brings further demand? What can they determine from how demand engages with different suppliers? How does Sarah feel about feedback systems?

5.) Why does Sarah believe that UGC plays are like marketplaces? What lessons can be drawn from TikTok to suggest this? How does Sarah think about her biggest lessons when analysing the growth of DoorDash? What do many not see that is important to recognise?

Item’s Mentioned In Today’s Episode

Sarah’s Favourite Book: Pachinko: The New York Times Bestseller

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20VC: Alexis Ohanian on Why Now Was The Right Time To Start Seven Seven Six, The 2 Very Distinct Types of Deals In Venture & The Unbundling of Social in 2021


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

Alexis Ohanian is the Founder @ Seven Seven Six, his new fund which just recently announced their first investment leading the $4M seed round for Dispo. Prior to founding Seven Seven Six, Alexis was the Co-Founder & Managing Partner @ Initialized Capital, where he backed many a unicorn including Ro, Flexport, Patreon, GOAT just to name a few. Alexis is also the co-founder @ Reddit, commonly referred to as the front page of the internet, their latest valuation priced the company at $3Bn.

In Today’s Episode You Will Learn:

1.) When Alexis left his L Sats to go get waffles, what did he learn about himself? How did that lead to founding Reddit? How did Reddit lead to angel investing? How did that lead to Initialized?

2.) Why did Alexis leave Initialized? Why was now the right time? What worked with Initialized that he has taken with him to Seven Seven Six? What did not work with Initialized that he has learned from? How does he view VC NPS as a result of this and the learnings?

3.) How does Alexis analyse his own relationship to money today? How did his relationship with his mother and her illness impact how he thinks about wealth and happiness? How did he feel when at 22 he sold Reddit? How does he feel about the “keeping up with the Jones'” mentality?

4.) How did having Olympia change how Alexis operates and invests today? How does Alexis define backing projects he would be proud to talk to Olympia about? How does he feel about the type of deals many investors make today?

5.) How did Alexis first meet PG from YC? How did he feel when he heard he believed in him and Steve with Reddit? How did that change how Alexis feels about being the first person to really back someone?

Item’s Mentioned In Today’s Episode

Alexis’ Favourite Book: Superforecasting: The Art and Science of Prediction

Alexis’ Most Recent Investment: Dispo

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20VC: Slack Founder Stewart Butterfield on Leadership Styles, Decision-Making, The 3 Levels of Wealth, IPOs vs Direct Listings & Why Effective Entrepreneurship is Like Parkour


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

Stewart Butterfield is the Founder & CEO @ Slack, the leading channel-based messaging platform, used by millions to align their teams, unify their systems and drive their businesses forward. Prior to their direct listing in June 2019, Stewart raised over $1.3Bn from the likes of Accel, Thrive, Softbank, Kleiner, IVP, T Rowe, GV and a16z to name a few. Prior to founding Slack, Stewart co-founded Flickr, a company he built into one of the largest web services in the world. Due to his many incredible successes, Stewart has been named to the 100 Most Influential People in the World by Time Magazine, and one of the Top 50 Leaders by BusinessWeek.

In Today’s Episode You Will Learn:

1.) How Stewart made his way into the world of startups and came to found Flickr? What was his founding moment for the Slack journey?

2.) How does Stewart think about and assess his relationship to money? How has it changed over time? What does Stewart believe are the 3 levels of wealth? How does Stewart think about his identity being tied to the company? Is that a challenge? How does he mitigate it?

3.) How does Stewart describe his management style and philosophy today? How has it changed over time? How does Stewart approach reversible vs irreversible decisions? How does Stewart structure post-mortems? Why does Stewart believe effective entrepreneurship is like parkour?

4.) How does Stewart think about and advise on the debate between direct listing, IPO and SPAC? What has been better/worse and different since making the transition to being a public company? What have been some of the biggest surprises?

5.) Why does Stewart believe that for most companies, comprehension is the reason for the lack of adoption and customer acquisition? How does he look to solve that with Slack? What have been their biggest mistakes on messaging and branding?

Item’s Mentioned In Today’s Episode

Stewart’s Favourite Book: Leadership and Self-Deception: Getting Out of the Box, Crucial Conversations Tools for Talking When Stakes Are High, The Courage To Be Disliked

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20VC: Accel’s Dan Levine on The Current State of Seed & Series A, The Rise of Pre-Emptive Rounds, Solo Capitalists and Multi-Stage Funds Entering Seed & Market, People and Product; What To Prioritise?


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

Dan Levine is a Partner @ Accel, one of the world’s leading venture firms with a portfolio including the likes of Facebook, Slack, Qualtrics, UiPath and Deliveroo. As for Daniel, he actually joined Accel in 2010 before leaving to join Dropbox. At Dropbox, he worked on the platform team helping open the platform to third-party developers and launched and managed many of the company’s developer-facing initiatives. Following Dropbox, he rejoined Accel and has led investments in Scale.ai, Mux, Vercel and Sentry to name a few.

In Today’s Episode You Will Learn:

1.) How Dan made his way into the world of venture with Accel? How that led to his joining Dropbox? What led to his re-joining Accel 3 years later?

2.) How does Dan assess the current state of the seed and Series A landscape? How does Dan analyse the rise of pre-emptive rounds? How does Dan determine when to lean in and pre-empt vs when not to? What does Dan think is the biggest myth about raising a Series A?

3.) How does Dan analyse multi-stage funds so actively entering seed? What has Accel’s seed portfolio data shown? How many went on to raise a Series A? How many did Accel lead? How many companies died? What is the biggest problem this portfolio presents?

4.) How does Dan analyse the trio of people, product and market? How does Dan approach market sizing? How does Dan approach the risk associated with market timing? What risk is he willing to take? What is he not? When can one stretch on market? When is it a stretch too far?

5.) How does Dan evaluate the rise of solo capitalists? What does he see as the core pros and cons of the model? What are the pros and cons of the partnership model like Accel has? How does Dan evaluate the rise of investor personal brands today? What worries him?

Item’s Mentioned In Today’s Episode

Dan’s Favourite Book: Titan: The Life of John D. Rockefeller, Sr. (Vintage)

Dan’s Most Recent Investment: Altinity

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20VC: Lessons from Investing in Uber and Airbnb, How To Think Through Bundling vs Unbundling, Late Stage Funds Moving Earlier, Early Stage Funds Moving Later& The Mechanics of Venture That Founders Should Know with Derek Zanutto, General Partner @ Capital


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

Derek Zanutto is a General Partner @ CapitalG, Alphabet’s independent growth fund with investments in the likes of Stripe, UiPath, Looker, Robinhood and Lyft to name a few. At CapitalG, Derek has led investments in Collibra, Dataiku and Armis as well as sitting on numerous boards. Prior to CapitalG, Derek spent a decade investing in such companies as Uber, Airbnb, Lynda.com and CAA at investment firms TPG, Hellman & Friedman and GIC.

In Today’s Episode You Will Learn:

1.) How Derek made his way from the world of TPG and growth equity to being a GP with Alphabet’s independent growth fund, CapitalG?

2.) Does Derek agree with Bill Gurley, “the biggest challenge is the over-supply of capital”? How does Derek see this changing with interest rate changes or lackof? How do interest rate changes impact later stage pricing? How does Derek assess his own relationship to price?

3.) How does Derek approach investments thinking through the bundling vs unbundling lens? What have been some core examples of this over the last decade? How does Derek assess market timing risk? What risks is he willing to take? How does he build a thesis ahead of meeting companies?

4.) What does Derek make of large later stage firms moving earlier and doing Seeds and Series A’s? What do entrepreneurs need to know about these firms? What does Derek think about early-stage firms scaling into multi-stage firms? Why is stage specificity so important?

5.) What are the core economics of venture capital that all entrepreneurs need to understand? How do different GPs and funds have different motivations according to fund size? How do different funds approach carry allocation and fees? Why does this matter to founders?

Item’s Mentioned In Today’s Episode

Derek’s Favourite Book: Sapiens: A Brief History of Humankind

Derek’s Most Recent Investment: Armis

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20VC: Zach Weinberg on Whether A Company is a Democracy, The Importance of Ownership, The Rise of Pre-Emptive Rounds, Multi-Stage Funds Entering Seed and How he Approaches Both Risk and Personal Capital Allocation


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

Zach Weinberg is a Co-Founder of Operator Partners, operators funding operators, with no outside LPs, just their own capital. Fun fact, 20VC Fund has actually invested with them in 3 companies from Alt, Dooly.ai and Boom Pay. Prior to founding Operator Partners, Zach was the Co-founder/COO of Flatiron Health (acq @Roche for $2b) and before Flatiron Zach co-founded Invite Media (acq @Google for $81m). If that was not enough, Zach has also been an incredibly successful angel in the past with a portfolio including RigUp, Ro, Color, BlueApron and Plaid to name a few.

In Today’s Episode You Will Learn:

1.) How Zach made his way into the world of startups, came to found Flatiron (acq for $2Bn) and how that led to Operator Partners?

2.) How does Zach analyse his own personal capital allocation? How much in funds? How much in cash, equities, direct, credit etc etc? How does Zach analyse his relationship to money? How has it changed over time? How does Zach evaluate his relationship to risk?

3.) What does Zach make of the rise of pre-empted rounds? When should founders takem them vs reject them? How does Zach feel about multi-stage funds re-entering seed aggressively? How does he advise founders? What are the pros and cons of having multi-stage money?

4.) How does Zach think about the importance of ownership? How does Zach analyse the re-investment decision? How does he approach reserve allocation? How does Zach reflect on his own price sensitivity? How has his relationship to price and ownership changed with time?

5.) How does Zach feel about Brian Armstrong’s piece on employees bringing their own political and external beliefs into the workplace? Why does Zach believe that companies are not a democracy? Why does Zach believe that we do not live in a democracy any longer?

Item’s Mentioned In Today’s Episode

Zach’s Favourite Book: Calling Bullshit: The Art of Skepticism in a Data-Driven World

Zach’s Most Recent Investment: David Energy

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20VC: The Implications of a Biden vs a Trump Administration on Venture and Startups, How The Rise of Rolling Funds, SPACs and Solo Capitalists Will Impact Venture & What We Can Do To Swing the Race Pendulum in VC with Barry Eggers, Founding Partner @ Ligh


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

Barry Eggers is a Founding Partner @ Lightspeed Venture Partners and currently Chair of the National Venture Capital Association (NVCA) Board of Directors. Lightspeed is one of the premier funds of the last decade with homeruns including Snapchat, Affirm, Mulesoft, Nutanix and Stitch Fix. Prior to LSVP, Barry spent close to 6 years as @ Cisco developing Cisco’s initial M&A program and leading the company’s first wave of acquisitions and integrations.

In Today’s Episode You Will Learn:

1.) How Barry made his way into the world of venture over 20 years ago and how he came to found one of today’s leaders, Lightspeed?

2.) What are the implications of a Biden administration? How does this compare to a Trump administration? What can be done to mitigate the tax concerns around Biden’s policies? How does Barry think about each candidate’s stance on immigration? What are the challenges here?

3.) How will SPACs change the world of venture? What will it take for them to be viewed in the same class as IPOs? Why are they often better than direct listings? How does the rise of solo capitalists change the state of venture? What does Barry make of rolling funds being born?

4.) What does Barry believe we can do to swing the race pendulum in venture? What were Barry’s biggest lessons in taking the Lightspeed partnership from 1 to 10 female partners? How can this be done with ethnic minorities also? What advice does Barry give to his counterpart GPs?

5.) How would Barry describe his own style of board membership? How has it changed over time? How does Barry keep his head in boards with many around him are losing theirs? What advice does Barry give to new board members adopting board seats for the first time?

Items Mentioned In Today’s Show:

Barry’s Favourite Book: Channel Kindness: Stories of Kindness and Community

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20VC: Unity Founder David Helgason on The Hypergrowth Early Days of Unity, Why Running A Company Is Like A Liberal Art, The Secret To A Successful CEO Transition and What Makes Roelof Botha Such A Special Board Member


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

David Helgason is the Founder @ Unity, the company that gives content creators the tools to create innovative RT3D experiences and deliver better processes for almost every industry. Prior to their IPO in 2020, Unity raised from the likes of Sequoia, Thrive, DFJ, SilverLake and then individuals including Max Levchin and VMWare’s Diane Greene. If that was not enough, David is currently a Partner @ Nordic Makers, a group of ten top Nordic angels working together to be the best angel investors in the Nordics. David also serves on the board of Labster, Realm.io and Quizup.

In Today’s Episode You Will Learn:

1.) How David made his way from founding Unity in a cafe in Denmark to the $10Bn+ public company it is today?

2.) How would David describe his leadership style? How has it changed over time? What were the biggest challenges David faced as the Founding CEO?

3.) What was the decision-making behind David’s transition out of the CEO role? What was challenging? What was key to make the transition successful? How did David know John Riccitiello was the right person for the role? How does David advise other founders contemplating the same?

4.) How does David analyse his own board management style? What are the most important elements a board member can do to help the company and founder? What makes Roelof Botha such a special board member to have? How does David advise new board members today to be successful?

5.) Why does David believe running a company is like a liberal art? How does David think about the importance of vision? How does David assess the current state of the European tech landscape? What can be done to improve it? How can investor approach change for the better?

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20VC: Sequoia’s Roelof Botha on His Biggest Lessons Working Alongside Don Valentine, Mike Moritz and Doug Leone, Leading Sequoia’s US Business and What Sequoia Do To Retain Their Edge at the Top & The Crucible Moments That Define Startup Success


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

Roleof Botha is a Partner @ Sequoia Capital, one of the world’s leading venture firms with a portfolio including the likes of Airbnb, Instacart, Stripe, UiPath, Zoom, the list goes on. As for Roelof, at Sequoia he has led rounds into the likes of YouTube, Instagram, Eventbrite, Square, MongoDB, 23andMe and Unity Technologies to name a few. Before joining the world of venture, Roelof was the CFO @ Paypal playing a key role in their hyper-growth from 2000-2003.

In Today’s Episode You Will Learn:

1.) How did Roelof go from actuary in South Africa to CFO @ Paypal? What were his biggest lessons from seeing Paypal burn $10M per month? How did Paypal lead to his joining Sequoia as a Partner?

2.) Market Evaluation: Does Roelof agree that the market is crazy today? How does today compare to prior vintages? How does Roelof assess the compression of fundraising timelines? With compressed timelines, how does he build relationships of trust with founders?

3.) Founder Evaluation: What were Roelof’s lessons on founder assessment from Don Valentine? What matrix did Don teach Roelof to assess founders on? How does Roelof feel about the rise of competitive rounds? When should founders take them vs remain heads down on execution?

4.) Investment Mentality: How did Roelof prevent becoming too confident when early investments went well? How does Roelof prevent relying on past failures as a reason for turning down opportunities today? What can investors do to retain a very flexible mind? Why does Roelof believe you are only as good as your next investment?

5.) Sequoia’s Edge: How does Roloef think about what it takes for Sequoia to retain it’s edge at the top? How does Roloef measure the success of the Sequoia scout program? How did they structure it? How has the structure changed? What do they plan to do moving forward?

6.) Board Membership: How would Roloef evaluate his current style of board membership? How has that style changed over time? What elements did he find challenging? What advice would Roelof give to new board members adopting their first board seats?

Items Mentioned In Today’s Show:

Roelof’s Favourite Book: Man’s Search For Meaning

Roelof’s Most Recent Investment: mmhmm

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20VC: Intercom Founder, Eoghan McCabe on How To Deal with the Weight of Expectation, Having Your Identity Tied To Your Company, How To Be Your Authentic Self Even with Stakeholders & Why There Are No Rules


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

Eoghan McCabe is a technology entrepreneur. He’s started a number of companies, the most notable of which is Intercom, the conversational relationship platform. He was CEO of Intercom for nearly 10 years, during which he grew the company to hundreds of millions in annual revenue, nearly 700 employees, and raised nearly $250M from the likes of Kleiner Perkins, Index, Bessemer, and ICONIQ. He’s also invested in dozens of companies including Stripe, Figma, SuperHuman, and Coda. In the summer of 2020 he moved to the role of Chairman of Intercom.

In Today’s Episode You Will Learn:

1.) How Eoghan made his way into the world of startups from Ireland and came to build one of the Valley’s greats with Intercom?

2.) How does Eoghan thinking about living and thriving with a chip on one’s shoulder? What does Eoghan advise in terms of one’s search for their true selves? What were his biggest learnings in his search? What does Eoghan advise people who maybe feel they have lost themselves?

3.) Having been CEO of a $Bn company for close to 10 years, how does Eoghan think about dealing with the weight of expectation placed on shoulders? How did he manage it? How does he think about his identity being so tied to his company?

4.) In terms of being one’s authentic self, how can one achieve this while also respecting their stakeholders who may hold different views? How does Eoghan think about being an authentic leader vs bowing down to the demands of your team? What is the right balance?

5.) Why does Eoghan think that vision can actually be limiting? How does Eoghan think about stress testing one’s vision and ambition? What adversity from early VCs did Eoghan have to fight against? How does Eoghan encourage dissent and debate within his teams?

Items Mentioned In Today’s Show:

Eoghan’s Fave Book: Breathe: simple breathing techniques for a calmer, happier life

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20VC: Cyan Banister on Her Relationship To Money, Risk, Her Investment Decision-Making Process, Why We Will See A Reckoning in the Early Stage Market, Her Biggest Takeaways from HQ Trivia & The Future of Silicon Valley


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

Cyan Banister is one of the most successful and renowned early-stage investors of the last decade. Her portfolio includes the likes of SpaceX, Uber, Affirm, Opendoor Postmates, Niantic and Thumbtack to name a few. Today Cyan is a Partner @ Long Journey Ventures, joining the team there following a 4-year stint @ Founders Fund where she led deals in both Niantic and HQ Trivia. Prior to Founders Fund, Cyan was a super successful operator and angel, co-founding Zivity and before that being an early employee at Ironport, leading to their acquisition by Oracle.

In Today’s Episode You Will Learn:

1.) How Cyan made her way into the world of startups? How SpaceX came to be her 1st angel investment? How that led to her joining the world of VC?

2.) How does Cyan think about and assess her relationship to money? Why does someone believe she had a fear or loathing of money? What made Cyan the capitalist she is today? How does Cyan analyse her relationship to risk? Has Cyan always trusted her own convictions?

3.) How does Cyan think about her own investment decision-making process? What were Cyan’s biggest lessons from her experience with HQ Trivia? How did she change how she interacts with founders pre-investment? Why does Cyan never Google someone before meeting?

4.) How does Cyan think about price sensitivity today? Why does she believe there will be a reckoning? How will this shake out in terms of who succeeds and who fails? Why is Cyan in favour of party rounds? How does she think about VCs with sharp elbows?

5.) Why does Cyan believe SF is eating itself? What can be done to reinvigorate the city positively? What can be done to solve much of the homelessness problem? Why does Chesa Boudin never convict anyone? Why does Cyan believe her “BLM tweet is not spicy”? Why is Cyan fundamentally sad and worried for the current state of the world?

Items Mentioned In Today’s Show:

Cyan’s Fave Book: Snow Crash

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20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

Spike Lipkin is the Founder & CEO @ Newfront Insurance, the modern insurance brokerage empowering risk management experts with advanced technology to deliver innovative solutions to their clients’. To date, Spike has raised from some of the best in the business including Founders Fund, Meritech and 20VC Fund. Prior to founding Newfront, Spike was one of the first employees at Opendoor, where he helped grow the team from 5 people to an enterprise value of over $5Bn today. Prior to Opendoor, Spike was an investor at Blackstone, where he served on the startup team that built Invitation Homes into the largest owner of single-family real estate in the United States.

In Today’s Episode You Will Learn:

1.) How Spike made his way from banking to be one of the first operators at Opendoor to founding the next generation of insurance with Newfront?

2.) What were some of the biggest takeaways for Spike from his time at Opendoor as employee #5? How does Spike approach prioritisation? How does he determine what to delegate vs what to control?

3.) How would Spike describe his own style of leadership? How has Spike needed to change his style with the business? What does Spike believe is his biggest weakness as a leader? What is he doing to confront it and grow as a leader? What is the most important thing a leader can do?

4.) How does Spike think about what it takes to acquire the very best talent? What does his framework for hiring look like? Why did Spike decide to hire a COO? Why was then the right time? How does Spike think about the balance between hiring external vs promoting internal?

5.) Why did Spike believe it was important not to announce any of his prior fundraises? How did Spike approach investor selection with Newfront? Does Spike believe founders should meet with VCs between fundraises? Which angel has done the most to move the needle for the company? How?

Items Mentioned In Today’s Show:

Spike’s Fave Book: Team of Rivals: The Political Genius of Abraham Lincoln

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20VC: CRV’s George Zachary on His Relationship To Money and How it has Changed Over Time, Why The Best Founders Have Often Experienced Parental or Home Instability and The Stories Behind Investing in Unicorns; PillPack, Yammer and Udacity


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

George Zachary is a General Partner @ CRV, one of the nation’s oldest and most successful early-stage venture capital firms with a portfolio including the likes of Airtable, DoorDash, Dropbox, Niantic and many more. As for George, today at the firm he focuses on advancing health through revolutionary computer science, centred around bio-engineering. During his incredible 16 year tenure at CRV, he has led deals in the likes of PillPack, Udacity, Scribd and HealthIQ. Before joining CRV, George was a General Partner @ Mohr Davidow Ventures for over 6 years.

In Today’s Episode You Will Learn:

1.) How George made his way into the world of venture over 21 years ago and how he came to be a General Partner @ CRV 16 years ago?

2.) How did seeing the booms and busts of the dot com and 08 impacts George’s investment mindset? What is the right way to voice concerns in an internal investment discussion? How does George now view capital intensity? How does it impact his conviction and check size?

3.) Why does George believe one should invest in founders who do not need their investors help? Why does George believe the best founders have experienced some form of parental instability? How does George detect the psychological need to win when he meets founders? What are the signs?

4.) How would George describe his own philosophy of board membership? How has it changed over time? What are the 2 control functions that a board member has? What advice does George give to new board members today? Where do many young board members make mistakes?

5.) How does George analyse his own personal relationship to money? How has it changed over the years? How did his relationship to money change his relationship with people? Was that challenging? How did he cope with it? How does he advise others who experience the same?

Items Mentioned In Today’s Show:

George’s Favourite Book: Foundation Trilogy

George’s Most Recent Investment: Glympse Bio

As always you can follow Harry and The Twenty Minute VC on Twitter here!

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20VC: CapitalG Founder David Lawee on Why People Overvalue Diversification in Venture, Why Investment Clubs Are More Successful Than Investment Partnerships & How Growth Funds Think About Portfolio Construction, Loss Ratio & Reserves


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

David Lawee founded CapitalG, Alphabet’s independent growth fund, in 2013, drawing on his experience both at Google and as a serial entrepreneur. Since then, he has helped transform high-potential startups into some of the most highly valued businesses of our generation, including Airbnb, Lyft, Snap, Robinhood, Credit Karma, Oscar, Lending Club and Thumbtack. Prior to CapitalG, David played a pivotal role in Google’s growth story–first as Google’s Chief Marketing Officer and then as the instrumental VP of corporate development where his group spearheaded over 100 acquisitions for the company.

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In Today’s Episode You Will Learn:

1.) How David made his way into the world of startups, came to be the first CMO @ Google and how that led to his founding CapitalG?

2.) Having operated and invested through both the dot com and 08′, how has seeing the booms and busts impacted David’s investing mindset? How does David think about temporal diversification today with CapitalG? Why does David believe diversification is largely overrated?

3.) How does David think about portfolio construction today, given CapitalG is a growth fund? How does David compare early-stage to growth today? How does David think about loss ratios at growth? How does David benchmark good vs great from a multiple perspective at growth?

4.) How does CapitalG approach investment decision making today? How does David avoid consensus thinking/following the crowd when it comes to deals? Why does David believe investment clubs operate much more successfully than partnerships? How does that change the structure for CapitalG?

5.) How has David seen himself evolve and develop as a board member of the years? What type of board member would David say he is today? How does that change with the founder? Who is the most memorable board member David has sat on a board with?

Items Mentioned In Today’s Show:

David’s Fave Book: Born A Crime: Stories from a South African Childhood 

David’s Most Recent Investment: Albert

As always you can follow Harry and The Twenty Minute VC on Twitter here!

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20VC: Arlan Hamilton: “We Have Come For Cake, Not The Crumbs”, Arlan’s Plan To Return $1Bn in 10 Years, Why Arlan Plans To Giveaway or Invest 90% of Her Wealth & What The LP Class Can Do To Ensure More Under-Represented Managers Get Funded


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

Arlan Hamilton is the Founder and Managing Partner @ Backstage Capital, the seed fund that has paved the way investing exclusively in startups that are led by underrepresented founders. Backstage Capital also expanded their model and now have Backstage Accelerator working with companies across 4 cities. Last month, Mark Cuban gave Arlan $6M to invest in underestimated founders (ArlanWasHere Investments Fund I). Arlan is also an Author of “It’s About Damn Time”. If you would like to invest with Arlan, you can, check out BackstageCrowd.com with over 2,000 accredited and non-accredited investors, they just completed their 6th deal and $1m raised within 3 months of launch.

In Today’s Episode You Will Learn:

1.) How Arlan made her way from the airport floor to founding her own venture firm, Backstage Capital and writing a book, “It’s About Damn Time”?

2.) How does Arlan assess her own relationship to money and wealth? What is Arlan’s thinking around her desire to give away 90% of her wealth? How does Arlan evaluate her own appetite for risk? How has that changed over time?

3.) From a strategic perspective, what are some core elements to Arlan’s strategy that are not obvious? What are the main misconceptions that remain with regards to under-represented founders? What does Arlan believe are the leading indicators when assessing founders today?

4.) What does Arlan believe have been the biggest challenges in building the firm that is Backstage? What have been the core breaking points in the scaling of people and strategy? How does Arlan think about the relationship between brand vs reputation? What does Arlan believe are the main misconceptions people have about her?

5.) How would Arlan like to see the world of venture change over the next decade? What can LPs do to encourage more under-represented founders are backed? How can this be measured? Who should be held accountable?

Items Mentioned In Today’s Show:

Arlan’s Fave Book: What I Know For Sure by Oprah Winfrey

As always you can follow Harry and The Twenty Minute VC on Twitter here!

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20VC: What Is Founder Narrative Fit and How to Detect and Invest In It, How To Avoid Consensus Thinking When Investing, Price Sensititivity; When To Pay Up vs Stay Disciplined & From New York Times To General Catalyst; Why Venture and Journalism are Not S


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

Katherine Boyle is a Partner @ General Catalyst, one of the leading venture firms of the last decade with a portfolio including the likes of Stripe, Snapchat, Airbnb, Canva, Cazoo, the list goes on. As for Katherine, at GC she has led deals in game-changing companies such as Anduril, Nova Credit, Spring Discovery and Airmap to name a few. Prior to General Catalyst, Katherine entered the world of venture with Founders Fund and before that spent an incredible 4 years at The Washington Post where Katherine investigated entrepreneurship in many forms.

In Today’s Episode You Will Learn:

1.) How Katherine made her way from investigating entrepreneurship at The Wall St Journal to being an intern at Founders Fund to today, being a Partner @ General Catalyst?

2.) Why does Katherine believe that journalism is like venture? Why does Katherine believe there are two different styles of venture? What were Katherine’s biggest takeaways from her formative years in venture with Founders Fund? How did that impact her investing mindset?

3.) What does Katherine mean when she says she “invests solely on founder narrative fit”? Are there leading indicators of this fit? What advice did Katherine take from her conversation with Mike Moritz pre VC career? How does Katherine strategically avoid consensus thinking and decisions?

4.) How does Katherine approach market sizing? How does Katherine think about strategic insertion into niches that expand to much larger markets? How does Katherine assess market timing? How does Katherine determine the velocity of a market tailwind? What is an example of this?

5.) How does Katherine evaluate the rise of pre-empted rounds today? What advice does Katherine give to founders considering taking multi-stage money at seed? Why did it make sense for Anduril? How does Katherine gain the time of the founders when they are not raising?

Items Mentioned In Today’s Show:

Katherine’s Fave Book: The Decadent Society: How We Became the Victims of Our Own Success

Katherine’s Most Recent Investment: Ophelia

As always you can follow Harry and The Twenty Minute VC on Twitter here!

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20VC: Anduril Founder, Palmer Luckey: “I Am Here To Build a $50Bn Company”, How Palmer Evaluates His Relationship To Money Pre & Post Oculus’ $2.3Bn Exit & Why The US DOD Needs To Be More Like China in It’s Approach


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

Palmer Luckey is the Founder @ Anduril Industries, founded on the premise of radically transforming the defence capabilities of the United States and its allies by fusing artificial intelligence with the latest hardware advancements. To date, Palmer has raised over $385M with Anduril from Founders Fund, a16z, Elad Gil, Spark Capital, Lux Capital, General Catalyst and 8VC to name a few. Prior to changing the world of defence, Palmer founded Oculus VR where he designed the Oculus Rift. Oculus VR was acquired by Facebook for $2.3Bn in 2014.

In Today’s Episode You Will Learn:

1.) How Palmer made his way into the world of startups, made his way from trailer to selling Oculus for $2.3Bn to changing the defence industry with Anduril today?

2.) How does Palmer evaluate his own relationship to money? How has that changed since his $2.3Bn Oculus exit? How does Palmer assess his relationship to risk? How does Palmer approach the correlations between money, risk and happiness?

3.) What were some of Palmer’s biggest takeaways from his time scaling Oculus? How have they informed his mindset with Anduril? What worked? What did not work? How has Palmer changed as a leader? How does Palmer approach personal development? How does he optimise for it?

4.) Palmer scaled Oculus to 1,400 people in 1 year, where do organisations break with scale? Why does Palmer believe, “you never want to play yourself”? Where does he feel his biggest weakness is as a scaling leader? How does Palmer approach hiring at scale yet maintaining culture?

5.) From a defence standpoint, why does Palmer feel the US needs to be more like the Chinese? Why is the DoD so poor at investing in innovation? What does it take to sell into the DoD really effectively? Why have the only 2 successful defence companies been founded by billionaires?

Items Mentioned In Today’s Show:

Palmer’s Fave Book: The Three-Body Problem

As always you can follow Harry and The Twenty Minute VC on Twitter here!

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20VC: The 4 Phases of Effective Decision-Making, The No 1 Quality of Good Decisions, How To Approach Effective OKR Setting, & How To Optimise and Improve Your Operating Cadence with Shishir Mehrotra, Founder & CEO @ Coda


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

Shishir Mehrotra is the Founder & CEO @ Coda, the startup that brings all of your words and data into a flexible all-in-one doc. To date, Shishir has raised over $140M from some great names including Greylock, Kleiner Perkins, General Catalyst, NEA and Homebrew to name a few. Prior to founding Coda, Shishir spent an incredible 6 years at Google in a couple of different roles; first as Director of Product for Youtube Monetisation and then moving to Youtube VP of Engineering, Product and UX. Before Google, Shishir was with Microsoft for 6 years as a Director of Program Management. Shishir also serves on the board of Spotify.

In Today’s Episode You Will Learn:

1.) How Shishir made his way into the world of tech, came to be VP of Engineering, Product and UX @ Youtube and how it led to founding Coda?

2.) What is the No 1 quality of a good decision? How does Shishir think through reversible vs irreversible decisions? What are the 4 phases of decision-making? When should decisions be based on speed vs not? How can teams adjust questions to come to more productive outcomes?

3.) How does Shishir encourage debate and dissent within team discussions? How can leaders build deep trust with their teams? How can leaders create true democracy for idea sharing and meritocracy? Should ideas always be acted on immediately? What are the pros and cons?

4.) How does Shishir think about and evaluate his own operating cadence? How has this changed over time? How does Shishir approach time allocation? What have been his core learnings? How does Shishir divide his time between proactive and reactive tasks?

5.) How does Shishir approach OKR setting? What can leaders do to create aspirational and inspirational goals? How should goals be correctly communicated across orgs? How many OKRs should one team/person have? How should attribution across OKRs be given?

Items Mentioned In Today’s Show:

Shishir’s Fave Book: Switch: How to change things when change is hard 

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

20VC: The Chainsmokers on Raising Their First $35M Fund and Entering The World of Venture, Dealing with Vulnerability and Insecurity Today & How Music and Venture Compare; The Similarities and Differences


This post is by Harry Stebbings from The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

Alex Pall and Drew Taggart are the Founders of The Chainsmokers and Mantis. The Chainsmokers are one of the most sought after musical acts of our time. As for Mantis, just last week they announced their first $35M venture fund and have backing from Ron Conway, Mark Cuban and Keith Rabois. They have already invested in hotly contested rounds for Fiton and Loansnap. Drew and Alex also own a production studio, are stakeholders in the spirit brand JaJa Tequila and last year co-founded the anti-scalper ticketing platform Yellowheart.

In Today’s Episode You Will Learn:

1.) How Drew and Alex made their way into the world of tech and startups and how they came to found a venture firm with Mantis?

2.) Why did Alex and Drew decide now was the right time for the fund? What did they look for in their LPs? How do they use their LPs to strategically help their companies? What is their preferred stage, sector? Do they have ownership requirements?

3.) Are Alex and Drew nervous about making the move into venture? If everyone has a chip on their shoulder, where does the chip on their shoulder come from? How do they think about their own vulnerabilities? How do they manage them? What works? What does not?

4.) What ways do Alex and Drew most like to work with their founders? Where do they provide outsized value? What are some examples of this? How do they think about working with VCs to get into the best rounds? How do they want to position Mantis in the ecosystem?

5.) With the tequila brand, the film production company and now the venture fund, how do they think about the expansion of “The Chainsmokers Empire”? What does this look like in 10 years? How would they like it to expand and grow?

Items Mentioned In Todays Episode

Drew’s Favourite Book: The Unbearable Lightness of Being

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.