20VC: Lightspeed’s Jeremy Liew on Being The First Investor in Snapchat, Why The Pessimism Around Consumer Is Wrong & Why Silicon Valley Is An Isolated Bubble and What Can Be Done To Change This

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Jeremy Liew is a Partner @ Lightspeed Venture Partners, one of the leading firms of the last decade with a portfolio including the likes of Snapchat, Mulesoft, Max Levchin’s Affirm, The Honest Company and many more incredible companies. As for Jeremy, he is best known for being the 1st investor in Snapchat and has also led investments in StitchFix, Affirm, Ripple, Giphy and Bonobos just to name a few. Previously, Jeremy was with AOL, first as SVP of corporate development and chief of staff to the CEO, and then as general manager of Netscape. Due to his incredible investing success, Jeremy has been featured on the Forbes Midas List multiple times.

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In Today’s Episode You Will Learn:

1.) How Jeremy made his way from AOL and Netscape to one of the most successful consumer investors of the last decade?

2.) How did the Snapchat deal come about? What did Jeremy see in the early Evan Spiegel that made him so excited? How has Jeremy seen him alter and grow with the company? What did the economics of the deal look like?

3.)Why does Jeremy disagree with much of the pessimism over consumer? How does Jeremy think about the lack of distribution channel availability with Google, Amazon, Apple owning them? How can this also present an opportunity in consumer?

4.) How does Jeremy think about price and price sensitivity? Would he agree with Peter Fenton on, “never turn down a deal based on valuation, it’s a mental trap”? How does Lightspeed think about reserve utilization? What does the conviction building process look like for reserve deployment?

5.) Jeremy has sat on the boards of Snapchat, Giphy, Bonobos and had 1,500 hours of board experience, so what makes the truly special board members? Who does Jeremy most like to work with on boards?

Items Mentioned In Today’s Show:

Jeremy’s Fave Book: World War Z

Jeremy’s Fave Blog: The Information

Jeremy’s Most Recent Investment: Rothy’s

As always you can follow HarryThe Twenty Minute VC and Jeremy on Twitter here!

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

Cooley are the global law firm built around startups and venture capital.  Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 50+ years working with VCs. They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund’s lifetime. So to learn more about the #1 most active law firm representing VC-backed companies going public. Head over to cooley.com and also at cooleygo.com.

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

20VC: How To Think About Founder-Category Fit, Why The Biggest Opportunities Are In Category Re-Architecture & What Can Be Done To Increase The Amount of Women In VC with Nadia Boujarwah, Founder & CEO @ Dia & Co

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Nadia Boujarwah is the Founder & CEO @ Dia & Co, the startup that provides premier plus size clothing and styling for women. To date they have raised over $20m in funding from some of the best in the business including the likes of Alfred Lin @ Sequoia and the team @ NextView Ventures. Prior to Dia&Co Nadia was the CFO and COO @ Frieda and Nellie and also enjoyed time in the marketing and strategy team @ Diane von Furstenberg.

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In Today’s Episode You Will Learn:

1.) How Nadia made her way from HBS grad to founding one of the hottest e-commerce companies of the day backed by Sequoia, Dia&Co?

2.) Why does Nadia believe that the biggest opportunity for value creation is through category creation? What does Nadia mean when she discusses category re-architecture? How does she think of the inherent cons (CAC, consumer education, distribution etc.)

3.) Despite the likes of Sequoia being invested now, the first year of Dia gained no institutional money. Why does Nadia think this is? What was the inflection point for VC interest? Is there anything that Nadia would change about how she has run the fundraising process?

4.) What does Nadia suggest as some core solutions to ensuring that more females become VCs? How does Nadia believe this will impact the types of companies that are being funded and built? What remain the core issues today?

5.) How does Nadia differentiate between customer centricity and customer devotion? Why is this so crucial in today’s proliferated world of e-commerce? How does Nadi and Dia determine with data, the extent to which they achieve their customer devotion targets?

Items Mentioned In Today’s Show:

Nadia’s Fave Book: Competing Against Luck

As always you can follow HarryThe Twenty Minute VC and Nadia on Twitter here!

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

Cooley are the global law firm built around startups and venture capital.  Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 50+ years working with VCs. They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund’s lifetime. So to learn more about the #1 most active law firm representing VC-backed companies going public. Head over to cooley.com and also at cooleygo.com.

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

20VC: Dick Costolo on The Balance of Vision and Realism in Startups, The Biggest Challenge in Scaling Twitter & How To Optimise Decision Making Internally

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Dick Costolo is the Chief Executive and co-founder of Chorus, a startup that is reimagining the path to personal fitness. Dick is also a Mentor @ Index Ventures, one of the world’s leading venture funds, which he joined in 2016. Costolo was most recently Chief Executive of Twitter from 2010 to 2015, where was at the forefront for their hypergrowth onto the main stage of tech. Prior to joining Twitter, Dick co-founded and ran three startups, including FeedBurner, which sold to Google in 2007. The former improv comedian has been a consultant on HBO’s “Silicon Valley” and currently sits on the boards of Patreon and IfOnly.

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In Today’s Episode You Will Learn:

1.) How Dick made his way from Improv Comedian to founding a startup acquired by Google and then becoming CEO of Twitter?

2.) Why does Dick believe that starting a company is like an improv stage? What were Dick’s biggest personal learnings from his drama career that he has applied to being a better leader today?

3.) Having given up the comedy dream for tech, how does Dick balance the entrepreneurial unwavering vision with a realism of when things are not working? What is the inflection point?

4.) What was the biggest challenge over the 5 years in scaling Twitter? What strategies did Dick utilise to combat this? How does Dick think about creating a culture of accountability without fear? How does this change the ownership of decisions?

5.) What is Dick’s biggest superpower and super weakness? Why must all entrepreneurs have to have a fundamental ability to compartmentalize? In terms of temperament, what were Dick’s biggest lessons from watching Youtube CEO, Susan Wojcicki, operate?

Items Mentioned In Today’s Show:

Dick’s Fave Book: Creativity Inc.

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

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

Cooley are the global law firm built around startups and venture capital.  Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 50+ years working with VCs. They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund’s lifetime. So to learn more about the #1 most active law firm representing VC-backed companies going public. Head over to cooley.com and also at cooleygo.com.

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

20VC: Why Vulnerability Is A Strength In VC, 3 Core Components That Make The Most Successful VCs & How VCs and Entrepreneurs Can Build Meaningful Relationships Pre-Investment with Brian Garrett, Founding Partner @ Crosscut Ventures

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Brian Garrett is the Founding Partner @ Crosscut Ventures, one of LA’s leading venture funds today with a portfolio including Super Evil Mega Corp, The Black Tux and Mobcrush just to name a few. Incredibly during the early days of Crosscut, Brian went back into a full-time operating role with a Public-company turnaround at Quepasa.com before co-founding vertical eCommerce brand StyleSaint.com. After surviving with the equivalent of two full-time jobs for roughly 6 years, Brian the attention of institutional capital, which enabled CrossCut to scale into a fund with $75M raised for CrossCut 3 in 2015. This has snowballed to their latest fund raised in December being $125m.

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In Today’s Episode You Will Learn:

1.) How Brian made his way into the world of VC and came to found one of LA’s leading funds in the form of Crosscut?

2.) What does Brian believe are the 3 core components that make for a successful VC? How important is the presence of humility for VCs today? How does Brian look to balance between arrogance and confidence? How is this shown in the entrepreneurial class?

3.) Why does Brian believe that vulnerability is actually a strength today? How can entrepreneurs be honest and vulnerable without ruining market perceptions and future fundraising aspirations?

4.) How does Brian look to place his relationship with the entrepreneur at the very core of every investment he makes? What does this relationship onboarding process look like? Is this possible in the fast-moving world of US deals today?

5.) What was the most challenging fundraise for Brian? Why was this case? How has he seen the evolution of Californian tech over the last few years since Fund III? What was the most memorable LP meeting for Brian?

Items Mentioned In Today’s Show:

Brian’s Fave Book: The Alchemist

Brian’s Most Recent Investment: Fuzzy Pet Health

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

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

Cooley are the global law firm built around startups and venture capital.  Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 50+ years working with VCs. They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund’s lifetime. So to learn more about the #1 most active law firm representing VC-backed companies going public. Head over to cooley.com and also at cooleygo.com.

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

20VC: The Biggest Growth Opportunities for Young People in Tech Today, Why Distributed Workforces Are The Secret To Beating Incumbents & Why It Has Never Been Easier To Operate A Company Than Today with Andy Pflaum, Founder & CEO @ Astro

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Andy Pflaum is the Founder & CEO @ Astro, the startup that brings email, calendar, and an AI-powered assistant together to help you focus on what’s most important. They have raised over $10m from leading West Coast investors such as Satish @ Redpoint, former guests Kent Goldman @ Upside and Michael Dearing @ Harrison Metal. As for Andy, prior to founding Astro, he spent 15 years in the valley, serving as the CMO @ Zimbra where he saw their immense scaling to their $350m acquisition by VMware where he then spent time on the other side of the table before moving to Chile to manage a family winery for 1.5 years.

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In Today’s Episode You Will Learn:

1.) How Andy made his way into the world of startups, made the transition to large corporates with VMware and Yahoo, came to run a Winery in Chile before founding Astro?

2.) Found a startup, work in early-stage startup or work at large incumbent; where does Andy believe young people today have the biggest growth opportunities? How does this mean emerging startups have to react to attain that talent?

3.) Why does Andy disagree with the notion that more and more incumbents are falling? Why is it harder than ever to compete against such a strong set of incumbents? What are the dangers of dependency on paid growth?

4.) How does Andy feel about distributed workforces? What is core to attaining the individuals and then scaling them successfully as a team, in a distributed fashion? How does Andy feel about hiring technical talent in the bay today?

5.) Why does Andy also argue, despite the incumbents, that it is also easier than ever to operate a business today What are the core changes that have allowed for this to happen? How does Andy break down the tech stack they use for Astro?

Items Mentioned In Today’s Show:

Andy’s Fave Book: The Wright Brothers

Andy’s Fave Blog: Tom Tunguz, Michael Dearing: Harrison Metal

As always you can follow HarryThe Twenty Minute VC and Andy on Twitter here!

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

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!