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

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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?

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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!

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20VC: Calm Founder Alex Tew on What It Takes To Build Viral Products Today, The Current State of Customer Acquisition Costs, What Makes The Best Brands

Alex Tew is the Co-Founder and Co-CEO @ Calm, the #1 App for Meditation and Sleep allowing you to find your calm, sleep more, stress less and live better. To date, the company has raised over $143M in funding from some of the best including Lightspeed, Insight, TPG and then some very cool names such as Ashton Kutcher, Harry Styles, Brad Feld and Jason Calacanis. Prior to Calm Alex founded numerous other startups including PopJam, Pixelotto and most famously rose to internet fame with his founding of The Million Dollar Homepage.

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In Today’s Episode You Will Learn:

1.) How Alex went from playing Fifa with Michael Acton Smith in Berwick St, London to founding one of the hottest startups in the valley, Calm?

2.) What does Alex believe the very best brands do today? How do they message? How do they present? How do they divide opinion? How did Alex think about the early Calm brand? How has it changed? How does Alex advise others looking to build a company brand?

3.) Does Alex agree with Peter Fenton, “there is a lack of free and open distribution”? How does Alex analyse the economics for customer acquisition costs today? What is a good paid vs organic ratio? How do CACS change over time in Alex’s experience?

4.) What have been Alex’s biggest learnings on what it takes to build a viral product? Where do many people go wrong? Why does Alex believe pressure is the enemy of creativity? Does Alex believe people should create time for creative thought? What does Alex do to stimulate idea creation?

5.) How has Alex seen himself evolve and develop as a leader over the last 5 years? What have been the hardest elements to scale? How does Alex think about effective delegation? What have been Alex’s biggest lessons on what it takes to hire A* people consistently?

Items Mentioned In Today’s Show:

Alex’s Fave Book: Godel, Escher, Bach: An Eternal Golden Braid

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

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20VC: a16z’s Angela Strange on Why Every Company Will Be A Fintech Company, How Founders Should Think About Niches and Optimal Insertion Points, How To Transition To Become The System of Record & Are We Entering A Period of Bundling Or Unbundling for Fintech

Angela Strange is a general partner at Andreessen Horowitz, one of the leading venture firms of the last decade with a portfolio including the likes of Facebook, Github, Slack, Airbnb, Asana and more. As for Angela, she largely focuses on investments in financial services and is currently a board member of Addi, SynapseFi, and Tally. Prior to a16z, Angela was a product manager at Google where she launched and grew Chrome for Android and Chrome for iOS into two of Google’s most successful mobile products.

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In Today’s Episode You Will Learn:

1.) How Angela made her way into the world of venture and came to be one of the leading fintech VCs with Andreesen Horowitz?

2.) Why does Angela believe that every company is going to be a fintech company? What is driving this shift? How does removing the barriers to entry for more products change both product quality and cost? How does Angela think about the role of regulation here?

3.) How does Angela think about what makes the best insertion points? How big does the initial wedge into the market have to be? When do you need to be able to prove you can transition from the insertion to the wider market? How does Angela fundamentally assess market size today?

4.) How does one transition to being the system of record? Do you have to be the system of record from day 1? Which examples are most striking for Angela on becoming a system of record? What are the biggest challenges in making this transition? Which metric tells you if you have become it?

5.) Does Angela think we are in a period of bundling or unbundling? What are the leading indicators of each? How does Angela assess the Fintech M&A market today? Will we continue to see large consolidatory moves in the form of Credit Karma, Plaid etc etc?

Items Mentioned In Today’s Show:

Angela’s Fave Book: Investing: The Last Liberal Art

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20VC: Biggest Lessons from Working with John Doerr, How Founders Can Have Discussions of Vulnerability with Their Board and Investors & Marrying Another Founder; The Pros, Cons and Ways To Make it Succeed with Alyson Friedensohn, Co-Founder & CEO @ Modern

Alyson Friedensohn is the Founder & CEO @ Modern Health, a one-stop solution for employee mental well-being through evidence-based support and digital content. To date, Alyson has raised over $45M in funding from some of the best in the business including Kleiner Perkins, Founders Fund, John Doerr, 01 Advisors and Katrina Lake to name a few. Prior to founding Modern Health, Alyson was a Product Partner for Operations at Collective Health and before that was an operations manager @ Keas (acquired by Welltok).

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In Today’s Episode You Will Learn:

1.) How Alyson made her way into the world of startups and came to change how we think about mental health with Modern Health?

2.) How does Alyson think about and assess her own psychology? How does Alyson deal with crisis modes? What works? What does not? What is the driver for Alyson to get her through the very toughest of times? How does Alyson approach her own attitude to risk?

3.) What is Alyson’s biggest pieces of advice for non-technical founders? What are the biggest challenges Alyson has had to overcome as a non-technical founder? How did she do it? How did Alyson strategically invest in the sales process? What worked? What did not? How does Alyson think about the balance of hitting sales quota and mental health?

4.) With some of the best VCs in the world, how did Alyson approach the process of investor selection? What can VCs do to build that relationship of trust with their founders? How does multi-stage VCs investing impact whether the founder remains in a “sales process” for the next round? How does Alyson temper the weight of John Doerr’s words?

5.) What have been Alyson’s biggest lessons in making it work marrying another founder? What works? What is challenging? How do they as a couple think about switching off? How does Alyson advise Harry on his own love life?!

Items Mentioned In Today’s Show:

Alyson’s Fave Book: How to Win Friends and Influence People

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

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20VC: SPACs. What Are They? Why Now? How Do They Change The Venture Landscape? Are They Better Than IPOs & Direct Listings? How Should Founders Think About Them? Kevin Hartz & Troy Steckenrider @ A*

Kevin Hartz is Co-Founder & Partner @ A*, a newly listed special acquisition company which raised $200M to acquire and take public a tech startup. Kevin is also the Co-Founder, former CEO, and Chairman Eventbrite (NYSE: EB). Before Eventbrite, Kevin was the Co-Founder & former CEO of online money transfer service, Xoom (acquired by PayPal for $1.1B). Kevin is also one of the most successful early-stage investors in the business with a portfolio including the likes of Airbnb (Seed, Series A), Uber (Series B), Pinterest (Seed, Series A), Trulia (first check) and PayPal (Seed).

Troy Steckenrider is Kevin’s co-founder and Partner @ A*. Prior to A*, Troy was COO @ ZeroDown changing the landscape for homeownership with $136M in funding. Before ZeroDown, Troy spent 5 years at Opendoor as Director of Capital Markets. Before that hyper-growth experience at Opendoor, Troy enjoyed roles at both Bain Private Equity and McKinsey.

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In Today’s Episode You Will Learn:

1.) How Troy and Kevin came together to co-found A*? What is a SPAC? What are Kevin and Troy looking to achieve with the SPAC?

2.) What does Kevin believe are the primary drivers for the rise in SPAC’s over the last few years? How will they change the structure of both the VC and startup industry? How will the SPAC landscape evolve over the next few years? What is the biggest challenge they face?

3.) Why does Kevin believe that the fee structure for SPACs is egregious? How would they like to change the incentive structure? How does the timeline for a SPAC transaction compare to that of an IPO? How does the fee structure compare when comparing SPACs to banks in IPOs?

4.) Why did Kevin and Troy choose $200M for the right size for their first SPAC? How does the size of the SPAC determine the type of company the SPAC will merge with? What are Kevin and Troy looking for in their partner company?

5.) What does the fundraising process look like for a SPAC? How do SPAC sponsors deal with the challenge that LPs call pull out if they do not like the proposed partner deal? When evaluating SPACs, what do investors look to invest because of? What makes A* special?

Items Mentioned In Today’s Show:

Troy’s Fave Book: Churchill: Walking with Destiny

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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