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

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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

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

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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!

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

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.

20VC: PagerDuty CEO Jennifer Tejada on A Leader’s Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like

Jennifer Tejada is the CEO @ PagerDuty, the company that provides a real-time operations platform ensuring less downtime for your digital services. Prior to their IPO in 2019 PagerDuty raised funding from some of the best in the business including Accel, a16z, Baseline, Bessemer and Harrison Metal to name a few. As for Jennifer, prior to PagerDuty, she was CEO of Keynote Systems leading to their acquisition by Dynatrace. Before Keynote, Jennifer was Executive Vice President and Chief Strategy Officer at Mincom, leading them to their acquisition by ABB. If that was not enough, Jennifer is also on the The Estée Lauder Companies Inc. (NYSE: EL).

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In Today’s Episode You Will Learn:

1.) How Jennifer made her way into the world of SaaS and came to be one of the leading enterprise CEOs today with PagerDuty? How does Jen advise graduates on joining a startup vs large incumbent?

2.) How does Jen analyse and evaluate her relationship to risk? What does Jen do to remove herself from her environment and make the clearest decisions? How has Jen’s decision making process changed? How does Jen encourage debate and free thought sharing internally?

3.) How does Jen think about the role of insecurity within leadership? What would Jen say are her biggest insecurities? How does Jen manage them and mitigate them today? What works? What does not? Why does Jen believe data is the key to overcoming insecurities?

4.) What have been Jen’s biggest lessons on what successful board management looks like? What separates good vs great board members? How can CEO’s structure their board in an optimal way? What do they need? What do they not need? How does scale change this?

5.) How does Jen think her style of leadership has changed over the years? What have been Jen’s lessons on what it takes to both acquire and retain the very best execs? Where do many go wrong here?

Items Mentioned In Today’s Show:

Jennifer’s Fave BookTuesdays With Morrie: An old man, a young man, and life’s greatest lesson

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: Sahil Lavingia on Rolling Funds and Their Impact on The Future of Venture, How To Evaluate Market, Team and Product, The Value of Party Rounds & The Pros and Cons of Multi-Stage Funds Investing at Seed

Sahil Lavingia is the Founder and CEO @ Gumroad, the company that helps creators do more of what they love. With Gumroad, Sahil has raised funding from an all-star list of investors including Accel, Kleiner Perkins, First Round and then Max Levchin, Chris Sacca, Ron Conway and Naval Ravikant on the individual side. However, most recently Sahil has made waves launching one of the first rolling funds on AngelList with his being $6M per year. In the past, Sahil has backed the likes of Lambda School, Figma, HelloSign and Haus to name a few.

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In Today’s Episode You Will Learn:

1.) How did Sahil make his way into the world of startups and angel investing? What were his biggest takeaways from being employee #2 at Pinterest? How did that experience impact his mindset?

2.) Why did Sahil decide to make his new fund an AngelList rolling fund? How is it structured? Does Sahil think this will represent a seismic shift in early stage investing? Is this a game of the 1%? Why does Sahil think early-stage remains so undervalued? How will this impact Series A pricing?

3.) How does Sahil assess his own price sensitivity today? How does Sahil think about the right way to turn down a founder? Where do many go wrong? How does Sahil feel about the rise of pre-empted rounds? How does Sahil advise seed founders with offers from multi-stage firms?

4.) What does Sahil believe founders care most about today in their investors base? How does Sahil think about investor brand and distribution? How does Sahil analyse the pros and cons of party rounds? How does Sahil advise founders on constructing their early cap table?

5.) How does Sahil think about his relationship to risk and to money? How did Sahil deal with it when his investors wrote off his company? How did Sahil feel about the weight of expectation placed on his shoulders at such a young age? How did he deal with this?

Items Mentioned In Today’s Show:

Sahil’s Fave BookHow to Win Friends and Influence People

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: Biggest Lessons From Scaling Houseparty To Millions of Users, Why Today’s Metrics Are Insufficient To Determine Product Success & What Breaks with Scale From Team To Product with Ben Rubin, Co-Founder @ /talk & Houseparty

Ben Rubin is the Founder & CEO @ /talk, the anti-meeting tool for fast, decentralised conversations. Prior to co-founding /talk, Ben was the Co-Founder & CEO @ Houseparty, where he scaled the product to millions of users and raised over $70M in funding from the likes of Sequoia, Greylock and Entree Capital to name a few. In addition over the last few years Ben has enjoyed roles at Sequoia as a Scout and then also at Benchmark as an Entrepreneur-In-Residence.

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In Today’s Episode You Will Learn:

1.) How Ben made his way into the world of startups and came to found Life on Air, later turning into Meerkat and Houseparty?

2.) What were Ben’s key learnings from the HOuseparty scaling experience? Why are the traditional metrics we use to measure startup success (DAU, MAU etc) insufficient? What are the nuance to metrics? How does Ben think about being first to market vs being the best to market?

3.) How does Ben believe the product principles differ when comparing the 0-1 stage vs 10-100 stage? How does Ben think about where to be rigorous on product? How does Ben advise founders to discover the key guiding product principle? What was it for Ben with Meerkat?

4.) Meerkat pivoted to Houseparty 3 months after having raised $40M, how did Ben communicate that to the board? How did they respond? How does Ben believe the best boards operate? What does Ben most look for in his board members? Where do many go wrong with board management?

5.) From the team side, when in hypergrowth, when do things start to break? What profiles are usually the first to break? Does that mean one should not hire those profiles? What can the leader do to create that intimacy and trust amongst the team?

Items Mentioned In Today’s Show:

Ben’s Fave Book: Seneca: The Shortness of 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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