20VC: If You Do Not Like VCs, You Have Not Worked With a Good One, How Andreesen Have Added The Same Level of Value As A Co-Founder, Why Market Is The First Thing To Consider When Angel Investing & Why Series A Is A Hiring Decision with Roger Dickey, Founder @ Gigster

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Roger Dickey is the Founder & CEO @ Gigster, the smart development service combining top developers and designers with artificial intelligence. They have raised over $30m in funding from the likes of a16z, Redpoint, Marc Benioff, Ashton Kutcher, Michael Jordan and then previous guests Rick Marini and Felicis Ventures. Prior to Gigster, Roger founded Mafia Wars, where he built the business to $1Bn in revenues and 100m users. Roger is also a prolific angel investor and LP in venture funds with a portfolio including the likes of Docker, ClassDojo and Addepar, just to name a few. If that was not enough Roger is also an advisor to 8VC, Lemnos Labs and OpenDoor.

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In Today’s Episode You Will Learn:

1.) How Roger made his way from founding Mafia Wars to changing the world of software development with Gigster?

2.) Roger has said before “if you dislike VCs, you have never worked with a good one”. So what makes a truly great VC to Roger? What does Roger believe are the core components VCs can add to a company? How should founders view investors when investing in them?

3.) Following Roger’s discussion with Mike Vernal, Partner @ Sequoia, why does Roger believe that the Series A is a hiring decision? How does this change how founders should think about the A round & present themselves throughout the round?

4.) Why does Roger think it is important for startup founders to invest in other startups? What benefits does this bring to you and your own company? How does Roger prioritize, time-wise between LP, GP and founder?

5.) When angel investing, Roger admits that he takes the “market first” approach. Why is this? How does Roger assess the element of market creation? How does Roger look to balance between founder first vs company first?

Items Mentioned In Today’s Show:

Roger’s Fave Book: On Intelligence

Roger’s Fave Blog: Elad Gil

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

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

If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic’s resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com

Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world’s best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

20VC: Why VCs Have Forgotten Their Job To Invest In Entrepreneurs not Technologists, How To Know When Growth Creates Value and When It Destroys It & How To Bootstrap Learning Most People Acquire Over Decades with 8VC Founding Partner, Drew Oetting

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Drew Oetting is a Founding Partner @ 8VC, one of Silicon Valley’s youngest and most exciting new entrants to the VC market with $425m for their debut fund. In just a few years they have built a portfolio including the likes of Oculus, RelateIQ, previous guest Elad Gil & Color, recent guest Mario @ Oscar and many more incredible companies. As for Drew, previously he served as Chief of Staff to fellow 8VC Founding Partner, Joe Lonsdale and was a two-time Bill Gates Investment Asset Management Fellow. Drew is also an advisor to Living On One, Rubicon Global and is a Founding Board Director @ Affinity Technologies.

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In Today’s Episode You Will Learn:

1.) How Drew made his way from Joe Lonsdale’s Chief of Staff to Founding Partner @ 8VC?

2.) Why does Drew believe the way we think of VC today will change? How does the extended period of privatization affect the role of the VC and their relationship to the founder vs the company?

3.) Why does Drew believe that funds make big mistakes in the internal setup of their operation? Why do funds not do a good job of developing talent? What are the problems of funds being internally competitive with deal by deal carry etc?

4.) As a Founding Partner of a $425m fund at 26, what were the challenges of having such a position, earlier than usual? How did Drew overcome them? What advice would Drew give to young people who want an accelerated career path?

5.) Why does Drew believe that “VCs have forgotten their job is to invest in entrepreneurs NOT technologists”? How does Drew determine whether someone has the ability to bridge both technologist and entrepreneur?

Items Mentioned In Today’s Show:

Drew’s Fave Book: Barbarians At The Gate, Fooled By Randomness

Drew’s Fave Blog: Dan Primack: Axios

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

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

If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic’s resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com

Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world’s best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

20VC: Benchmark’s Eric Vishria on Why Career VCs Have Advantages Most Under Appreciate, Why We Are In An Infrastructure Renaissance & What Makes The Best VC Partnership

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Eric Vishria is a General Partner @ Benchmark, one of the world’s leading VC funds with a portfolio including the likes of Twitter, Uber, Snapchat, eBay, WeWork, Yelp and many more revolutionary companies of the last decade. At Benchmark, Eric has led deals and sits on the board of the likes of Confluent, Amplitude, and Bugsnag. Prior to being in VC, Eric was the Founder & CEO @ Rockmelt, the startup that sought to re-imagine the browser for the way people use the web today, the company was ultimately acquired by Yahoo in 2013. Prior to Rockmelt Eric held numerous different roles including VP of Products @ HP and VP of Marketing @ Opsware.

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In Today’s Episode You Will Learn:

1.) How Eric came to be one of the 5 GP’s at Benchmark following operational success with Rockmelt, HP and Opsware?

2.) Why does Eric believe the pendulum has swung too far to the operational route into VC? What are the under-appreciated benefits of career VCs and the perspective they bring? How does Eric expect the pendulum to swing in the coming years?

3.) What makes the best-performing venture partnerships? How does Benchmark think about partner composition and career pre-VC? How does Benchmark structure investment decision-making? Why do they favor advocacy over unanimity?

4.) What does Eric mean when he says we are at the beginning of an infrastructure renaissance? What opportunities does this create in the venture landscape? How does this lead Eric to consider the current state of the consumer landscape?

5.) How does Eric view multi-stage investing? Why does Eric and Benchmark favour stage specifity when it comes to investing? What are the dangers of larger stage funds investing in earlier rounds for optionality?

Items Mentioned In Today’s Show:

Eric’s Fave Book: Endurance: Shackleton’s Incredible Voyage To The Antarctic

Eric’s Most Recent Investment: Confluent 

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

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

If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic’s resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com

Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world’s best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

20VC: Raising Over $700m From The World’s Best Investors, How To Innovate In Highly Regulated Markets & The 3 Superpowers of Insurance Companies with Mario Schlosser, Founder & CEO @ Oscar

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Mario Schlosser is the Founder & CEO @ Oscar, the startup that makes health insurance easy. They have raised over $700m in funding from some of the world’s best investors including the likes of Founders Fund, Google Capital, Thrive Capital, Lakestar, Khosla Ventures and Jim Breyer just to name a few. Previously, Mario co-founded the largest social gaming company in Latin America and held roles with the likes of Bridgewater Associates and McKinsey. Fun fact, as a visiting scholar at Stanford University, Mario wrote 10 computer science publications, including one of the most-cited computer science papers published in the past decade.

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In Today’s Episode You Will Learn:

1.) How Mario made his way into the world of healthcare and Oscar from founding Latin America’s largest social gaming company?

2.) Why is insurance one of the most complex spaces in tech? Why is there a chance for companies, not governments, to cut costs and innovate on the current system? Does Mario agree with Brian Singerman, “once we go to a single player, innovation ends”, thesis?

3.) Oscar has raised over $700m, to what extent does Mario believe that too high a valuation can be a liability? How did Mario look to select his investors? What are the challenges of raising funds for a category-defining opportunity?

4.) Oscar now has over 600 in the team, where have been the inflection points in the scaling of the company? Where have things broken? How does Mario look to rectify and observe these inflection points ahead of time?

5.) How does Mario look to optimise team composition? How does he look to balance athletes with heavy domain experts? Does Mario believe that too much domain expertise can prevent innovation due to a lack of naivety?

Items Mentioned In Today’s Show:

Mario’s Fave Book: Herr Lehmann

Mario’s Fave Blog: Spiegel

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

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

If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic’s resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com

Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world’s best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

20VC: Why Core AI Is Largely A Bunch of Nifty Tricks, Why Consumer Electronics Is The Hardest Thing To Do In Venture & Why Silicon Valley Will Dominate The Future of Robotics with Jeremy Conrad, Partner @ Lemnos Labs

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Jeremy Conrad is a Partner @ Lemnos Labs, the fund that believes in the earliest stages of building hardware, every dollar counts, every hour matters and every decision is crucial to success or failure. Consequently, Lemnos invests in pre-seed and seed hardware startups encountering these very real challenges. Among their portfolio is the likes of previous guest Swift Navigation and Airware, just to name a few. As for Jeremy, prior to VC he was in the United States Airforce where he was in charge of an $80m tests and targets group and was also responsible for the BMC4I system of the Airborne Laser (ABL).

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In Today’s Episode You Will Learn:

1.) How Jeremy made his way from the United States Airforce to investing in the next generation of great hardware founders with Lemnos?

2.) Why does Jeremy believe that now is the time for robotics? What megatrends mean now is the right time? Why does Jeremy believe that core AI today is largely a bunch of nifty tricks?

3.) Why does Jeremy believe that Silicon Valley will dominate the future of robotics? What characteristics does the valley have that mean this is the case? What is the dirty secret of Silicon Valley?

4.) How does Jeremy view the funding environments for hardware? Where is there constrictions of capital for hardware startups? What must hardware founders have in place in order to raise a Series B?

5.) Why does Jeremy believe that consumer electronics is the hardest space for venture today? With the likes of Juicero and Pearl, is consumer still possible today? Are the likes of GoPro and FitBit merely anomalies in the dataset?

Items Mentioned In Today’s Show:

Jeremy’s Fave Book: The Better Angels of Our Nature 

Jeremy’s Fave Blog: Dan Primack: Pro Rata

Jeremy’s Most Recent Investment: Marble

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.

If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic’s resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com

Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world’s best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

20VC: Index’s Mike Volpi on Making The Move From Player To Coach, What It Takes To Build Generation Defining Brands & How Europe Really Stacks Up To The US Venture Market

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Mike Volpi is a General Partner @ Index Ventures, one of the world’s leading venture funds with a portfolio including the likes of Facebook, Dropbox, Slack, Supercell and Deliveroo just to name a few. Mike currently sits on the boards of prior guests, Cockroach Labs and Wealthfront, as well as Blue Bottle Coffee, Sonos and Zuora just to name a few. Prior to Index, Mike was a director @ Cloud.com (acq by Citrix) and StorSimple (acq by Microsoft). Before that, Mike held a number of executive positions including Chief Strategy Officer at Cisco. He also serves on the board of Fiat Chrysler Automotive.

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In Today’s Episode You Will Learn:

1.) How Mike made his transition from operator and M&A exec to General Partner @ Index and opening their West Coast Office?

2.) Question from Dave Morin @ Slow: How did Mike’s childhood in Italy and Japan affect how he views and interacts with entrepreneurs today? Question from Danny Rimer: How has Mike found the transition from player to coach with the move to VC?

3.) Question from Andy Rachleff: Having seen both the US and European venture markets, how do they compare? Why does Mike think being an entrepreneur in Europe is far more solitary? What does it take to create a VC brand, like Index in an already very crowded West Coast market?

4.) Having had a front-row seat for the brand building of the likes of Sonos, Blue Bottle and Eero, what does Mike believe are the core tenets to building generation-defining brands? How has this changed over the last 5-10 years?

5.) Does Mike agree with Rob Siegel that the enterprise market is now less exciting given we might be entering a period of consolidation? Why does Mike believe this actually represents opportunity? How will we see open source play a role in the next wave of these enterprise companies?

Items Mentioned In Today’s Show:

Mike’s Fave Book: Undaunted Courage 

Mike’s Fave Blog: The Information

Mike’s Most Recent Investment: Eero

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

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

If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic’s resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com

Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world’s best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

20VC: Litecoin Founder, Charlie Lee on Why ICO’s Are The Biggest Threat To Crypto, Why Ethereum Will Run Into Huge Scalability Problems & How To Assess The Trade Off Between Decentralisation & Scale

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Charlie Lee is the creator of Litecoin, the most popular alternative currency to Bitcoin, which Charlie created as a side project in 2011 while working at Google. Today Litecoin has a market cap of $3.29Bn. As well as creating Litecoin, Charlie has also been the Director of Engineering @ Coinbase, working alongside recent 20VC guest and Coinbase founder, Brian Armstrong. Prior to this, Charlie held roles at Microsoft, Google and Guidewire.

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In Today’s Episode You Will Learn:

1.) How Charlie made his way from Google to Coinbase to founding Litecoin in his free time? What were Charlie’s biggest takeaways from being at Coinbase?

2.) What does Charlie believe is the biggest barrier to the world of cryptocurrency and BTC? What is the holy grail to securing this and the future of the space within mass consumer usage?

3.) How does Charlie think about the largest problem for crypto and BTC, scaling? Why does Charlie believe that Ethereum will have large problems scaling? How does Charlie assess the balance of centralization, scaling and transaction efficiency?

4.) Why is Charlie’s biggest concern the current ICO market? Why does he believe it is the “wild west”? What happens to alternative currencies when the ICO market crashes? Who are the ultimate winners in the ICO markets?

5.) How does Charlie analyse the differing communities when comparing ETH to BTC to LTC? Does community serve as a core form of IP for currencies and their stability moving forward?

Items Mentioned In Today’s Show:

Charlie’s Fave Book: Game of Thrones

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

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

If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic’s resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com

Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world’s best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

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