Semil Shah is the founder of Haystack, an early stage investment firm now investing out of it’s fourth fund, with previous investments in the likes of Instacart, DoorDash, Giphy, OpenDoor & Managed by Q. Semil is also a Venture Partner @ GGV Capital, one of the leading multi-stage funds and in the past he has also been a consultant to the likes of Kleiner Perkins, DFJ, General Catalyst and more. If that was not enough, Shah also has an extensive career in media having been a contributor for both TechCrunch and the Harvard Business Review in the past. Due to all of this, Shah is known for being on the speed dial of some of the industry’s most respected VCs with the likes of Marc Andreessen naming him one of his ’55 Unknown Rockstars in Tech’.

In Today’s Episode You Will Learn:

1.) How Semil made the transition from the world of writing to investing alongside some of the best in venture with Haystack?

2.) Why do more and more managers want to introduce institutional capital into their LP base? What are the advantages? What are the drawbacks? Where does Semil see most managers going wrong when pursuing institutional capital for the first time?

3.) What does Semil mean when he states the importance of "pre-marketing"? How open is one in these pre-discussions with potential LPs? What is the right amount of time to be pre-marketing for? How does Semil determine whether to adopt a piece of LP advice and when not to?

4.) In the raising process, why does Semil never like to the use the deck when meeting in person? What core elements of the presentation did LPs always hone in on? What tips does Semil have to potential managers to ensure they can pitch at any time, not just the boardroom?

5.) How has moving from non-institutional to institutional fund, changed how Semil thinks about reserve allocation? Why does Semil believe that the majority of LPs have a wrong thesis to reserve allocation?

6.) Why does Semil believe the VC business model is severely constrained in terms of exits through IPO and acquisition? What does this mean for the use of secondaries? How will managers need to incorporate this into their strategy?

Items Mentioned In Today’s Show:

Semil’s Fave Blog: AVC 

Semil’s Most Recent Investment: Ironclad

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

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

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Julia Hartz is the Co-Founder & CEO @ Eventbrite, the unicorn startup that is the world's largest event technology platform, powering over 2 million events around the world each year. They have raised over $330m from some of the greats of industry including Roelof Botha @ Sequoia Capital, Jeff Clavier @ SoftTech, David Saks, Bebo's Michael Birch, Tiger Global and many more. Under Julia's leadership, she has taken Eventbrite to become the world's largest event technology platform and has received multiple accolades for workplace culture, being named the best place to work in SF for 7 years running. Personally, Julia has won numerous awards including Fortune's 40 Under 40, Inc's 35 Under 35 and Most Powerful Female Entrepreneurs.

In Today’s Episode You Will Learn:

1.) How Julia came to found Eventbrite with her husband Kevin from a small apartment in Potrero Hill and turned it into the unicorn it is today?

2.) How did Julia and Kevin meet? What was the meet-cute? How did that translate into the founding of Eventbrite? How did Julia think about partnering with her fiancee at the time, as a business partner? What made it also a great business partnership?

3.) Why does Julia believe that creating a company is like creating a family? How has Julia seen herself scale as CEO of the company, with the immense scaling and growth of the firm? What have been the challenges and how did she overcome them?

4.) What does Julia believe are the requirements for successful CEO transition? How can this be managed correctly both internally and externally? What other elements made last year a particularly momentus year for change at Eventbrite?

5.) How does Julia think about balancing the immediate elements of the present day with the long-term vision for the roadmap? What is the right mindset to adopt? How does one look to prevent "Innovators Dilemma"? How does Julia split her time?

Items Mentioned In Today’s Show:

Julia’s Fave Book: Overwhelmed

Julia's Fave Blog: The Skimm

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

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

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Sam Arbesman is the Scientist-In-Residence @ Lux Capital, the fund that supports scientists and entrepreneurs who pursue counter-conventional solutions to the most vexing puzzles of our time, the more ambitious the project, the better. Sam works with companies and founders that recognize the future happens at the boundaries of science and technology infusing computation into everything from biology to manufacturing.Sam’s scientific research has been published in everything from the Wall Street Journal to The New York Times and The Atlantic. Sam is also the author of the award-winning The Half-Life of Facts and the new book Overcomplicated: Technology at the Limits of Comprehension.

In Today’s Episode You Will Learn:

1.) How Sam made his move from being a best-selling author to Scientist in Residence for Lux Capital? As Scientist in Residence, what does Sam do on a day-to-day basis?

2.) What does Sam mean when he says that startups need to embrace "radical interdisciplinarity"? What really is "radical interdisciplinarity"? What are the benefits it brings to an organisation? Does this go contra the importance of specialisation?

3.) How does Sam view the partnership between man and machine? Why does Sam believe we will see computational creativity in a way never seen before? How does Sam view the societal barriers to the embracing of this partnership?

4.) How does Sam view the promise of analogizing in the face of such complex systems? How does Sam assess the perils of such analogies? Does Sam believe that VCs of today are equipped to invest in such complex systems? What must they remember?

Items Mentioned In Today’s Show:

Sam’s Fave Book: The Baroque Cycle by Neal Stephenson, The Three Body Problem

Sam's Fave Blog: Marginal Revolution

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

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

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Aaron VanDevender is the Chief Scientist at Founders Fund, one of the world's leading fund with investments in the likes of Facebook, Airbnb, SpaceX, Spotify and many more incredible companies. At Founders Fund, Aaron monitors the scientific impact of the portfolio, works with portfolio companies, assesses new technologies, and conducts his own research. Prior to Founders Fund, Aaron has designed single-photon and single-atom quantum computers in academia and government (NIST), advanced the quantum-mechanical theory for microscopic black holes, patented the fastest transparent optical switch, and is a co-inventor of yoctotechnology. He then developed next-generation DNA sequencing technology at Halcyon Molecular. His broad scientific interests encompass energy, biotech, nanotech, and computing.

In Today’s Episode You Will Learn:

1.) How Aaron made his way from microscopic black holes and DNA sequencing to the world of Founders Fund? What does a Scientist-In-Residence do?

2.) Why does Aaron believe that AI is mostly a scam? Where does Aaron see and then want to see further progression in the field of AI and ML? How does Aaron distinguish between crazy and genius? What are the signs?

3.) Why does Aaron believe that the value of massive datasets is largely overplayed? What characteristics of datasets are exciting for Aaron to see when evaluating an opportunity? Where and how can datasets be misleading and lose their value?

4.) How does Aaron view the societal effects of 4m truck drivers being unemployed by the rise of self-driving? How does Aaron view trucking both as goods distribution and wealth distribution networks?

5.) How does Aaron view the implementation of universal basic income? Why does Aaron believe we have a challenge decoupling wealth and virtue? To what extent is this a core problem?

Items Mentioned In Today’s Show:

Aaron’s Fave Book: Tales From The Thousand & One Arabian Nights

Aaron's Fave Blog: Slash Dot

Investment Aaron is Most Excited By: Ayar Labs

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

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

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Luis Von Ahn is the Founder & CEO @ Duolingo, the leading language learning platform with over 100m users. They have backing from some of the best in the investing world with over $100m in funding from the likes of USV, Kleiner Perkins, NEA, Google Capital and even Ashton Kutcher. Prior to Duolingo, Luis is known for inventing CAPTCHAs, being a MacArthur Fellow (“genius grant” recipient), and selling two companies to Google in his 20’s. Luis has been named one of the 10 Most Brilliant Scientists by Popular Science Magazine, one of the 20 Best Brains Under 40 by Discover.

In Today’s Episode You Will Learn:

1.) How Luis, a man as he describes "never great at learning languages", came to found the leading language learning app, Duolingo?

2.) Why do VCs generally believe Edtech to be such a "hard" space? Is that really a fair assumption? How does the role of government change the distribution and landscape of edtech? How does content creation play a pivotal role in edtech today?

3.) What role does Luis believe AI and ML will play for the future of edtech? Will the transition to bots represent a transformational shift in the interface paradigm? How does gamification and edtech integrate? Why does Luis always measure themselves against the most addictive of games?

4.) How has Luis seen himself scale and change as a leader with the scaling of the firm? What story shows an element that Luis struggled with and how did he overcome it? What were the major inflection points in the growth of the firm?

5.) Duolingo recently raised their $25m Series E, how did this round differ from prior rounds? Why did they want to negotiate down the figure they wanted to raise? How did Valley based VCs present herd mentality for the duration of the recent raise?

Items Mentioned In Today’s Show:

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

Luis' Fave Blog: AVC by Fred Wilson

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

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

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Samir Kaji is what one might call, a master of all things seed stage and micro VC financing. Over his 18 years in venture capital, Samir has assisted or advised over 700 companies and 300 VC firms and has completed tech financing transactions totaling over $4.0 billion in committed capital. Today, Samir is the Senior Managing Director @ First Republic Bank where leads the technology banking team managing venture capital and startup company relationships. He joined First Republic in 2013 from Silicon Valley Bank, where he was also a managing director.

In Today’s Episode You Will Learn:

1.) How Samir made his entry into the world of VC from the ground up and has come to advise and assist on over $4Bn worth of capital commitments?

2.) Where is the micro VC and seed market today? What is the overview? What has fundamentally changed over the last few years? Are all increases in capital supply good or is this too much? Why is Samir concerned by valuation bloat at seed?

3.) How are LPs reacting to this explosion in seed and micro fund managers? How does this differ when assessing the differing classes of LP from institutions to HNWs and family offices? What are the likelihoods of 1st-time funds attaining institutional capital?

4.) How should potential managers think about the right fund size to raise? How long a timeline should be given to the raising of micro and seed funds? What exceptions are there to this timeline? How does the role of multiple closings play into this timeline?

5.) How does Samir differentiate between raising a fund and building a franchise? What does this mean about how a certain set of anagers not only engages in the fundraising process but also depicts the narrative?

Items Mentioned In Today’s Show:

Samir’s Fave Book: Hard Thing About Hard Things

Samir’s Fave Blog: Strictly VC, AVC by Fred Wilson

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

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

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Michael Dearing has established himself as an icon of early-stage venture over the last decade. With his founding of Harrison Metal in 2006, he has backed the likes of Twitter, MoPub, Birchbox, 99Designs and PagerDuty just to name a few of his incredible companies. Prior to being in VC, Michael spent 6 years at eBay across numerous roles and before that held positions at Shoe Warehouse as CEO, The Walt Disney Company in corporate strategy and then Bain & Co as a consultant.

In Today’s Episode You Will Learn:

1.) How Michael made his way into the world of venture from selling shoes with Shoe Warehouse to eBay to founding his own fund?

2.) Michael has said before that he looks for "personal exceptionalism" within the teams he backs, what does that really mean? How does he distinguish brilliance from arrogance? What is the balance between vision and stubbornness?

3.) How does Michael think about price sensitivity? How does he use it as a determining factor to test his level of conviction in the deal? More broadly, how does Michael view pricing in the market today? Why are the convertible debt markets so toxic?

4.) How does Michael view strategy around reserve allocation? Why does Michael believe reserves are where he has made the biggest mistakes? What are his takeaways from those mistakes? Why does recycling not feature as a core tenet of his strategy?

5.) Why does Michael believe that "benevolent dictatorship" is a beautiful thing? Does this thesis change in the debate over founder vs company first? How does Michael use McCallum's 5 key principles to assess founders and their ability?

Items Mentioned In Today’s Show:

Michael’s Fave Book: Confederacy of Dunces

Michael’s Most Recent Investment: Astro

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

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

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Sami Inkinen is the Founder & CEO @ Virta Health, the startup on a mission to reverse type 2 diabetes for 100m people by 2025. They have raised over $35m in funding from the likes of Max Levchin, Ev William's Obvious Ventures, Paypal, Ray Tonsing @ Caffeinated Capital and previous 20VC guest, Bob Kocher @ Venrock. Previously, Sami was a co-founder, COO and President of Trulia until it’s IPO and eventual sale for $3.6B. Sami, an avid athlete, is a triathlon world champion in his age group, and recently rowed across the Pacific Ocean from California to Hawaii unsupported with his wife at a record speed to raise awareness about healthy nutrition.

Bram Sugarman is the Director of Corporate Development & Strategic Partnerships at Shopify, the e-commerce titan that has over 500 merchants in 150 countries on their platform. Prior to joining Shopify, Bram was a venture capitalist with OMERS Ventures, the venture capital arm of one the largest pension funds in the world. As a VC, Bram worked on more than 20 transactions helping the OMERS Ventures grow from 1 investment to 24 investments. Bram helped lead and manage OMERS Ventures' investments in Shopify (IPO), HootSuite, VidYard, PasswordBox (Acquired by Intel), BusBud, Hopper, League, and AppHero (Acquired by Fuse Powered).

In Today’s Episode You Will Learn:

1.) How Bram made his way into the world of VC and then jumped to the other side of the table, buying startups with Shopify?

2.) What does using corporate development as a platform to accelerate product roadmap mean? How does this mean it differentiates from traditional M&A? How does Bram work with product team in the M&A process? What are the benefits of doing this?

3.) How does Bram assess the attractiveness of acquihires? What are the 2 differing types of acquihires? What are the essential characteristics of the individuals in those acquihire situations?

4.) With integration being the biggest risk of M&A, what does the ideal post-acquisition process look like? What must be done on both the side of the startup and the acquiror to make the process as smooth as possible?

5.) With regards to pricing and valuation, why does Bram urge founders to consider the long term and what does that mean? How can founders determine the truth with regards to long term objectives of their acquiror?

Items Mentioned In Today’s Show:

Bram’s Fave Book: Einstein by Walter Isaacson

Bram’s Most Recent Acquisition: Oberlo

As always you can follow Harry, The Twenty Minute VC and Bram 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.

Matt Switzer is the Senior Vice President of Strategy and Corporate Development @ Hootsuite, the social media management platform that has raised venture funding from some of the best in the world including Accel, Insight Venture Partners and Fidelity. At HootSuite, Matt and his team have raised over $250m in funding, acquired 8 companies and launched 4 new products. Prior to Hootsuite, Matt was on the other side of the table as a VC, where he helped to establish a new fund and manage an incubator.

In Today’s Episode You Will Learn:

1.) How Matt made his way into the world of VC and then decided to jump to the other side of the table as acquirer with Hootsuite?

2.) What is the build, buy or partner thinking process? When analysing markets, what does that deep dive and examination look like and entail? How does Hootsuite identify and select startups within the identified markets?

3.) How does Hootsuite most like to interact with startups in pipe? What does the relationship building look like? What platforms and tools are used to monitor those relationships post initial meeting?

4.) What does the internal conviction building process look like around a potential deal? What is the traditional structure of such a deal? How does Matt assess price sensitivity and it's ties to product market fit achieved by the startup?

5.) From the other side of the table, when should startups look to be building their M&A pipe? In conversations with potential acquirers, what are the foundations for them to remember? What role do VCs play and value do they provide in these conversations?

Items Mentioned In Today’s Show:

Matt’s Fave Book: Red Notice

Matt’s Fave Blog: Tom Tunguz

Matt’s Most Recent Acquisition: AdEspresso 

As always you can follow Harry, The Twenty Minute VC and Matt 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.

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.

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.

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.

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 Harry, The 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.

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.

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 Harry, The 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.

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).

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 Harry, The 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.

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.

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 Harry, The 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.

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 is also 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.

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 Harry, The 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.

Kathleen Utecht is a General Partner @ Core Innovation Capital, I would say one of the most under the radar but immensely exciting funds in market and they are looking to revolutionize financial services with their portfolio. With their portfolio are the likes of NerdWallet, PayJoy, fundera and Mayvenn just to name a few. Prior to Core, Kat was an investor at Comcast Ventures and WVP Ventures. Prior to her venture roles, Kath invested in and led Green Rock Entertainment, an online/offline commerce startup. Before that, Kat cut her teeth in the world of finance working as an investment banker at Raymond James.

In Today’s Episode You Will Learn:

1.) How Kat made her way from car entrepreneur dreams to operator to now, General Partner @ Core?

2.) Why does Kat believe that "society is on a downgrade"? Does Kat agree with the Thiel thesis of "we expected flying cars and were given 140 characters"? Where does Kat most want to see entrepreneurs spending their time and skills?

3.) How does Kat view regulation with regards to startup operations and expansion? Why does Kat believe that "sector specific funds should be in every highly regulated deal"? What are the core benefits? How can VCs really aid with regulation?

4.) Kat has previously said that "VC is a lifestyle not a job", what does Kat mean by this? How does this mean VCs should behave with regards to founder interactions and communications? How can entrepreneurs stress test whether a VC has this belief?

5.) How does Kat view the process of losing companies? What does her post mortem analysis look like? Why does Kat believe that if you do not lose companies, you are not taking enough risk?

Items Mentioned In Today’s Show:

Kat’s Fave Book: Atlas Shrugged

Kat’s Fave Blog: AVC by Fred Wilson

As always you can follow Harry, The Twenty Minute VC and Kat 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.

Andy Weissman is a Partner @ Union Square Ventures, one of the world’s leading VC firms with investments in Twitter, Twilio, Zynga, Soundcloud, Tumblr, Lending Club and many more. At USV, Andy sits on the boards of YouNow, ScienceExchange, Figure 1 and previous guest, CircleUp. Prior to joining USV, in 2007 he co-founded betaworks, which both created and invested in social, real-time applications and services. You can also check out Andy's fantastic blog here.

In Today’s Episode You Will Learn:

1.) How Andy made his way into the world of startups and investing, came to found Betaworks and then made the move to USV?

2.) Andy has previously said the business "is more about luck than skill and process rather than foresight". Why does Andy place so much emphasis on process? How has Andy seen his process evolve over the years? How does the process of an individual balance with the process of the firm?

3.) Why does USV not agree with voting as a method of investment decision making? How do Andy and USV approach reserve allocation? What model and simulators do they use to determine which companies receive follow on funding?

4.) Why does Andy believe that recycling cash from early exits is good for everyone? How has Andy found that LPs respond to this? What is the balance? What is the right amount for recycling, 110%, 120% or 130%?

5.) How does Andy view price sensitivity? To what extent does Andy agree with Peter Fenton that "valuation is a mental trap"? Has there been a time when Andy has lost a deal due to price? How has that changed his psyche and approach to the topic?

Items Mentioned In Today’s Show:

Andy’s Fave Book: On The Road by Jack Kerouac

Andy’s Fave Blog: Phish.net, Continuations, Radio Free Mobile

Andy's Most Recent Investment: Flip

As always you can follow Harry, The Twenty Minute VC and Andy 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.

Jon Callaghan is a founder of True Ventures, one of the West Coast's leading early stage funds with a portfolio including the likes of Fitbit, recent unicorn Peloton, Automattic (makers of Wordpress) and more amazing companies. Jon also led the deals and sits on the board of Fitbit, Brightroll, Peloton and Glu Mobile, just to name a few. Prior to True, Jon founded 3 of his own companies, the first being in 1986 with Mountain Bike Outfitters Inc. Following several years founding companies, Jon made his move into VC with Summit Partners and then enjoyed roles with AOL's venture incubator, CMGi's Venture group and Globespan Capital.

Phil Black is a founder of True Ventures, one of the West Coast's leading early stage funds with a portfolio including the likes of Fitbit, recent unicorn Peloton, Automattic (makers of Wordpress) and more amazing companies. Prior to True, Phil learnt the craft of venture at Summit Partners and at the predecessor firm to Lightspeed Venture Partners. However, it was in 2003 that Phil co-founded a small angel fund, Blacksmith Capital with the mission to prove his thesis that great founders of early stage technology companies can and often prefer to start their businesses and get a lot of traction with $2.5 million or less of initial funding.

Tim Harris is the Founder & CEO @ Swift Navigation, the startup focused on building a world-class organization that will power the next generation of GPS-enabled robots and autonomous vehicles. They have raised over $45m in VC funding from some of our favourites including the likes of First Round, Felicis, Lemnos Labs and NEA. As for Tim, prior to Swift Tim held numerous roles from supply chain consulting to corporate finance encapsulating strategic partnerships and M&A.

Alina Cohen is a General Partner @ Initialized Capital, one of Silicon Valleys leading early stage seed funds. Their portfolio includes the likes of recent unicorn, Coinbase, Flexport, Cruise Automation, OpenDoor and many more incredible companies. As for Alina, prior to Initialized, she ran tech investments for Tamares Group, the first outside investor in Palantir, and previously founded Recrec, a computer vision startup which was acquired by Facebook, where she worked on Platform and Groups.

In Today’s Episode You Will Learn:

1.) How Alina made her way from selling her computer vision startup to Facebook to GP with one of SF's best new seed funds, Initialized?

2.) Why does Alina think gaming is so similar to start-ups? What core components are the same? What about gaming led Alina to realise there were secrets to the world of starting companies and growing startups in Silicon Valley?

3.) Why is Alina so focused on engineering-centric founders? Why does Alina feel they are the most attractive investment opportunities? Why are they the founder profile that deals best when pivots have to be made?

4.) Why does Alina think that AI is more artificial than intelligent today? If ML is a "leveraged play on data", where are the opportunities for startups with such data incumbency? Does AI just help the big get bigger?

5.) Why is Alina so bullish on the future of personal voice computing? What does Alina think will be the catalyst to consumer adoption? What are the compelling consumer applications with voice? Why does this remind her of the early FB platform days?

Items Mentioned In Today’s Show:

Alina’s Fave Book: The Three-Body Problem

Alina’s Most Recent Investment: Fly.io

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

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

Pendo delivers the only complete platform that helps companies create great products. The Pendo Product Experience Platform enables product teams to understand product usage, collect user feedback, measure NPS, assist users, and promote new features in-app – all without requiring any engineering resources. This unique combination of capabilities helps companies improve customer satisfaction, reduce churn, and increase revenue. Pendo is the proven choice of Salesforce, Cisco, Optimizely Citrix, BMC and many more leading companies. Start a free trial at http://go.pendo.io/harry

Treehouse is an online school where you can learn how to build websites and apps. Their course library has thousands of hours of content, where you can learn all sorts of topics, including Javascript, iOS, Android and more.  With high-quality video instruction from real industry experts teaching you all you need to know, and quizzes and code challenges keep you engaged and on track. Learn on your own schedule and go from beginner to pro. Go to teamtreehouse.com to start your free trial.

Mike Jones is the Co-Founder & CEO @ Science Inc, one of America's most successful incubators with an incredible 3 Science Inc portfolio companies exiting in 2016 alone with the sales of Dollar Shave Club, Hello Society (acquired by NYT) and Famebit (acquired by Google). Science continue to push the frontier of tech with their recent announcement of Science Blockchain, the first ICO blockchain incubator ever, with the ICO pre-sale starting in just 13 days from now. Prior to Science, Mike was the CEO @ MySpace, where he was responsible for one of the most high-profile turn-around challenges in the industry.