20VC: Arlan Hamilton: “We Have Come For Cake, Not The Crumbs”, Arlan’s Plan To Return $1Bn within 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

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.

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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 BookWhat 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 So Different with Katherine Boyle, Partner @ General Catalyst

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.

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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 BookThe Decadent Society: How We Became the Victims of Our Own Success

Katherine’s Most Recent Investment: Ophelia

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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

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.

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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 & Why Your Operating Cadence is the Backbone of Your Culture with Shishir Mehrotra, Founder & CEO @ Coda

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.

To check out the incredible resources and core themes discussed by Shishir in the episode, check it out here.

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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

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.

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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!

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20VC: Lambda School Founder, Austen Allred on How To Assess Your Relationship To Risk and Money, Why San Francisco Is A Case Study For The Greatest Squandering of Wealth in History & Why Complexity Increases Exponentially with Scale

Austen Allred is the Founder & CEO @ Lambda School, the startup that remotely trains people to become a web developer or data scientist and the students pay no tuition until they are hired. Just last month, Lambda’s $74M Series C was announced led by Gigafund bringing their total funding to date to over $129M with prior investors including Stripe, Bedrock, GV, Gigafund and GGV to name a few. Prior to founding Lambda, Austen was Senior Manager for Growth @ LendUp and before that co-founded Grasswire.

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In Today’s Episode You Will Learn:

1.) How Austen made his way into startups having slept in a Honda Civic and how he went from homeless to rockstar founder @ Lambda?

2.) How does Austen evaluate his own attitude to risk? How does Austen think about downside protection today? How has this changed over time? How does Austen feel about founders taking secondaries? How does Austen think about his own relationship to money?

3.) Having raised his Series C last month, why did Austen choose the investors he did? How did the round progress? What made Gigafund different to alternate options? What makes the best board members in Austen’s mind? What makes the worst?

4.) What have been the most challenging elements for Austen of scaling the team? How does complexity change with time in team scaling? Why did Austen bring in a COO? What did he look for in the role? How does Austen advise others on brining in a COO?

5.) Why does Austen believe that post-COVID we will never go back to the valley as we knew it? Why does Austen believe the valley represents the biggest potential squandering of wealth in history? How does Austen evaluate the government intervention we have seen?

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: Sequoia’s Ravi Gupta on His Lessons From The Hyper-Growth of Instacart, The Key Question To Ask When Building or Evaluating Teams & The Importance of Investing In and Detecting Slopes Rather Than Intercepts

Ravi Gupta 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 Ravi, prior to Sequoia, he spent 4 years as COO & CFO @ Instacart playing an integral role in their hyper-growth journey. Before that Ravi spent 10 years as a Director @ KKR.

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In Today’s Episode You Will Learn:

1.) How Ravi made his way from KKR to being one of the key execs leading Instacart? How Instacart led to Ravi becoming a Partner @ Sequoia?

2.) When thinking about team, what does Ravi believe is the single most important question to ask? How does Ravi determine between good and great when assessing talent? What are the leading indicators? What have been Ravi’s lessons on what it takes to acquire those great talents?

3.) How does Ravi think about and approach prioritisation today? How does Ravi analyse what to delegate vs what to control? Should you get good at your weaknesses and double down on strengths? How does Ravi think about vulnerability within leadership? How did he show that vulnerability as a leader at Instacart?

4.) In joining Sequoia, what has Ravi been most impressed with in regards to the team? What has he been most surprised by? Why is Ravi so bullish unanimous decision-making is right? How do founders determine which Sequoia Partner will be on their board?

5.) How does Ravi think about what it takes to be the very best board member? Who is the best board member Ravi has worked with? What made them so special? What advice does Ravi give to new board members adopting board seats for the first time?

Items Mentioned In Today’s Show:

Ravi’s Fave Book: Clay Christensen: How Will You Measure Your Life?

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.

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