Dennis Mortensen is the CEO and Founder of X.ai, the artificial intelligence driven personal assistant that lets people schedule meetings using plain English and nothing more than a CC to amy@x.ai. Their female persona Amy is so lifelike that users have asked her on a date at a rate of one request per month! X.ai is now one of the best funded AI startups having raised over $30m from our friends at FirstMark and DCM and a big thanks to Matt Turck for making the intro and from DCM, who also helped us with some of the questions for Dennis!

In Today’s Episode You Will Learn:

1.) How Dennis came to found one of the leading AI startups today with X.ai?

2.) Why is product market fit like porn? How does this analogy affect Dennis' evaluation of product market fit?

3.) What are the fundamental features required to turn a single user consumer product into an enterprise product? How should that transition be managed?

4.) Is Dennis concerned by large incumbents making their entrance into the world of more traditional enterprise companies with the likes of GSuite and Facebook for Work?

5.) How did Dennis evaluate the right pricing method for X.ai? What pricing mechanisms did he consider? What does Dennis believe is the future of enterprise pricing?

Items Mentioned In Today’s Show:

Dennis' Fave Book: Shoe Dog

Dennis' Fave Blog or Newsletter: Azeem Azhar: The Exponential View

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

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

X.ai is AI-poweredered personal assistant for scheduling meetings bringing you Amy or Andrew. The assistant you interact with like you would to any other person and it allows you to avoid the tedious hours of email ping pong in order to schedule one meeting. Even better, there is no sign in, no password, no download, all you do is cc amy@x.ai beautiful! And you can check it out now on x.ai it really is a must!

Workable is the all-in-one recruiting software for ambitious companies. From posting a job to tracking and managing candidates, Workable provides everything you need to hire better. Transparent communication, organized candidate profiles, structured interviews and a full reporting suite gives hiring teams the information they need to make the best choice. Workable is available for desktop and mobile and you can find out more on workable.com where you can try it for free.

Roger Ehrenberg is the Founder and Managing Partner @ IA Ventures, one of New York’s leading early stage funds with investments in the likes of TransferWise and The Trade Desk. Prior to IA, Roger was a prolific angel investor making investments in over 40 companies including BuddyMedia and previous guest, Howard Lindzon’s StockTwits. Before that, Roger served as President and CEO @ DB Advisors, Deutsche Bank’s internal hedge fund trading platform which managed $6Bn in capital across multiple geographies.

In Today’s Episode with Roger You Will Learn:

• How Roger made his way into VC from the world of Wall St?
• How does Roger view the diversification model of 50+ in a portfolio in micro VC? What levels of ownership does that require?
• With regards to small and honed portfolios Roger has previously said that ‘small is beautiful’. How does Roger approach this with IA and what capital pools does this allow his partners?
• Roger has also said that ‘VC platforms are not a panacea’. What does he mean by this? What do founders really want from an investment partner today?
• What is the effect of Roger and IA being outside the traditional echo chambers of Silicon Valley? How does this affect Roger’s dealflow? Hiring ability? Partnership opportunities?

Items Mentioned In Today’s Show:

Roger’s Fave Blog and Newsletter: Maria Popova: BrainPickings

Roger’s Fave Book: Out Of The Crisis

Roger’s Most Recent Investment: Octane Lending

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

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

X.ai is AI-powered personal assistant for scheduling meetings bringing you Amy or Andrew. The assistant you interact with like you would to any other person and it allows you to avoid the tedious hours of email ping pong in order to schedule one meeting. Even better, there is no sign in, no password, no download, all you do is cc amy@x.ai beautiful! And you can check it out now on x.ai it really is a must!

Workable is the all-in-one recruiting software for ambitious companies. From posting a job to tracking and managing candidates, Workable provides everything you need to hire better. Transparent communication, organized candidate profiles, structured interviews and a full reporting suite gives hiring teams the information they need to make the best choice. Workable is available for desktop and mobile and you can find out more on workable.com where you can try it for free.

Scott Belsky is a Venture Partner @ Benchmark, one of the world's leading VC funds. As an early-stage investor himself he has made investments in the likes of Uber, Warby Parker, Pinterest and Flexport just to name a few. Prior to Benchmark, Scott co-founded Behance in 2006, and served as CEO until Adobe acquired Behance in 2012. After Behance's acquisition, Scott served as Adobe's Vice President of Products, rebooting Adobe's mobile product strategy and leading Behance until 2016. If that was not enough Scott is also, the co-founder and Chairman of a new marketplace product under development.

In Today’s Episode You Will Learn:

1.) How Scott made his move into VC with Benchmark having founded Behance and been a VP @ Adobe?

2.) How did Scott see his investment decision making process change when comparing being an angel to a VC? What was it about VC that made Scott realise that he would not be a traditional VC?

3.) Why does Scott believe that when momentum is growing too fast it is generally likely to fade out? At what point is the transition point between large momentum that is and is not sustainable?

4.) Why is Scott fascinated by 'the journey in between'? What gives Scott hope when reviewing a company in this stage? What does he always look for?

5.) Why does Scott think that autonomous vehicles in cities will be a public utility? Will the data sets produced be publicly or privately owned? Who will operate mass transit systems?

Items Mentioned In Today’s Show:

Scott’s Fave Book: Tribe: On Homecoming & Belonging

Scott’s Fave Blog or Newsletter: The Information

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

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

X.ai is AI-poweredered personal assistant for scheduling meetings bringing you Amy or Andrew. The assistant you interact with like you would to any other person and it allows you to avoid the tedious hours of email ping pong in order to schedule one meeting. Even better, there is no sign in, no password, no download, all you do is cc amy@x.ai beautiful! And you can check it out now on x.ai it really is a must!

Workable is the all-in-one recruiting software for ambitious companies. From posting a job to tracking and managing candidates, Workable provides everything you need to hire better. Transparent communication, organized candidate profiles, structured interviews and a full reporting suite gives hiring teams the information they need to make the best choice. Workable is available for desktop and mobile and you can find out more on workable.com where you can try it for free.

Jeremy Johnson is the Founder & CEO @ Andela, the startup that aims to bring a scientific approach to building engineering teams. They have backing from some of the best investors in the world with the likes of the Zuckerberg-Chan Initiative, Spark Capital, Google Ventures and our friends at Susa Ventures just to name a few. As for Jeremy, prior to founding Andela, Jeremy co-founded 2U, one of the fastest-growing education technology startups in history. 2U went public in 2014 (NASDAQ:TWOU) and continues to transform higher education. Jeremy has spoken on education and entrepreneurship at meetings hosted by the White house and Congress and was named “30 Under 30” by Inc. Magazine in 2012 and Forbes in 2013 and 2014.

In Today’s Episode You Will Learn:

1.) How Jeremy made his entry into startups and came to found Andela?

2.) Question from Paige Craig: How did the Zuckerberg-Chan Initiative deal come about? What has been the effect of taking that round for the company and for you as the founder?

3.) How does Jeremy view the contrast between being CEO and being founder? What does he believe makes a truly great CEO?

4.) Andela is an intensely operational and logistics based business, how did Jeremy learn to handle this? What were the fundamental challenges?

5.) How does Jeremy view the future wof work? Why does Jeremy believe the future can only be in decentralised work forces?

Items Mentioned In Today’s Show:

Jeremy’s Fave Book: The Power of One

Jeremy's Fave Blog or Newsletter: Social Snippets, Charles Hudson @ Precursor

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.

Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Intercom.com/20MVC

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.

Ben Blumenfeld is the Co-Founder & General Partner @ Designer Fund, they invest in startups co-founded by designers and build and educate design teams through their program, Bridge. Designer Fund's portfolio includes the likes of Gusto, Stripe, Shyp, Operator and many more incredible companies. As for Ben, previously Ben was a design lead at Facebook for over 5 years where he helped build products for nearly a billion people and grow Facebook’s world-class design team. He was also the design director at Varien which he helped build into one of the world’s leading e-commerce firms.

In Today’s Episode You Will Learn:

1.) How Ben made the move from designer to General Partner @ Designer Fund?

2.) How does Ben's design background inform how he invests in companies and then supports them post-investment? How does he evaluate design opportunities from the design perspective?

3.) Why now has design become such a competitive advantage in tech? What has changed? What are the fundamentals of beautifully designed products today?

4.) How does Ben believe the current crop of VCs view design? What do they not understand? What should they look to understand? Will we see a new class of design-centric VCs?

5.) From seeing the likes of Facebook, Medium and Asana scale deign teams, what have been the takeaways to effectively scaling design teams with the growth of an organisation? What is required for this to be successful?

Items Mentioned In Today’s Show:

Ben’s Fave Book: The Power of One

Ben's Fave Blog or Newsletter: Social Snippets, Charles Hudson @ Precursor

Ben’s Most Recent Investment: Hustle

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

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

Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Intercom.com/20MVC

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.

Pejman Nozad is the Founding Managing Partner @ Pear.vc, one of the leading seed stage funds in the valley. However, Pejman did not enter the tech industry like most venture capitalists. Having immigrated from Iran, he lived in an attic above a yogurt shop and took a job at a rug store in the Valley. But he immersed himself in what was happening in technology. Slowly, with a few small investments, he developed a reputation for identifying talent and helping take promising ideas to the next level. From next to nothing, he built a $20B portfolio, investing in over 100 startups and seeding several multi-billion dollar companies such as Dropbox, Lending Club, SoundHound and Gusto.

In Today’s Episode You Will Learn:

1.) How Pejman made his way from football in Iran to rug dealer in Palo Alto to leading seed stage VC?

2.) Mike Moritz has previously said that 'a call from Pejman is a call he will always take'. What led Mike to say this? What makes Pejman the brilliant networker and community builder that he is?

3.) How does Pejman assess early stage founders and teams? From seeing an early Andy Rubin, what did Pejman take from that as to what makes the best founders?

4.) Pejman invested $400K in Andy Rubin's Danger which exited 8 years later for $500m yet Pejman only 2x his money. What did he take from this? What have been the other major learning inflection points for Pejman in the journey?

5.) From working alongside some of the best investors of our generation, what does Pejman perceive to be the commonalities of the best investors? How do they operate? How do they evaluate early stage opportunities?

Items Mentioned In Today’s Show:

Pejman’s Fave Book: Power of Now

Pejman's Most Recent Investment: Gfycat

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

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

Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Intercom.com/20MVC

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.

Micah Rosenbloom is Managing Partner @ Founder Collective, one of the leading seed funds in the world with investments in Uber, Buzzfeed, Makerbot, PillPack, Coupang and Cruise, just to name a few. As for Micah, prior to VC with Founder Collective, his career was varied starting as a Hollywood agent before becoming a serial entrepreneur founding 3 companies with the last, a successful exit alongside his now Partner Eric Paley with Brontes Technology. Micah also is a Board Member with Sequoia Funded Dia and Co and board observer with both MoveWith and Sense360.

In Today’s Episode You Will Learn:

1.) How Micah made the move from Hollywood agent to leading seed stage VC?

2.) Why does Micah believe it is wrong to have themes to invest against? Why does he believe that the most interesting businesses can be found in weird and wonderful places?

3.) Why does Micah believe it is a problem for founders to focus exclusively on top line valuation? Why does Micah disagree with the common notion that a $100m exit is not exciting for VC?

4.) Why does Micah believe it is wrong for founders to build their company for the next round? Why does Micah disagree with Jason Lemkin in stating, 'the best investors know the benchmarks clearly for the next round'. 

5.) How does Micah deal with the fire hose of activities inherent within venture? How does he prioritise those activities? What thesis does he base all his decisions around?

Items Mentioned In Today’s Show:

Micah’s Fave Book: Thinking Fast and Slow

Micah’s Most Recent Investment: Skysafe

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

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

Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Intercom.com/20MVC

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.

Topher Conway is a Co-Managing Partner of SV Angel, one of Silicon Valley's leading seed funds with investments in the likes of Facebook, AirBnB, Twitter, Dropbox and many more. At SV Angel, Topher works particularly close with Gusto, Github, Lookout and many more incredible companies. He was included in Forbes Magazine's 30 Under 30 in 2015. Prior to SV Angel, he worked at EQAL, Inc. At EQAL, he worked with the Business Development and Sales teams and lead efforts in creating new business opportunities. Prior to EQAL, he held positions at eCost and a 2004 summer internship in Google's Direct Sales Organization. He is also a member of the UCLA VC Fund, helping foster entrepreneurship at the University.

In Today’s Episode You Will Learn:

1.) How Topher made his way into the wonderful world of VC and came to be Managing Partner @ SV Angel?

2.) How has the rise of the pre-seed market affected Topher's access to deals? How has Topher reacted to the creation of this new market segment with their new fund size?

3.) How does Topher evaluate grit within founders? Do Topher and SV prefer serial or first-time founders? How does Topher and SV approach startup pivots? Where is the line between stubbornness and vision?

4.) To what extent does Topher focus on valuation and ownership? Why does he believe that it is not important at this stage? What is his determinant to see whether it will be a problem?

5.) To what extent has Topher witnessed the Series A Crunch? Where does he see gaps in the investment landscape? Why does Topher not have a problem with bridge rounds?

Items Mentioned In Today’s Show:

Topher’s Fave Book: The Score Takes Care Of Itself

Topher's Most Recent Investment: BetterUp

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

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

Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Intercom.com/20MVC

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.

Gautam Gupta is the Founder & CEO at NatureBox, the startup that allows consumers to discover new & healthy foods through a monthly subscription service. They have raised over $50m in VC funding from the likes of General Catalyst, Redpoint, SoftBank and many more. Prior to launching NatureBox, Gautam was a Principal at General Catalyst Partners. While at General Catalyst, he sourced and was actively involved with the firm’s investments in GoodData, Bigcommerce, Honest Company and many more. Gautam joined General Catalyst from Procter and Gamble, where he analyzed brand strategy and consumer preferences in the Consumer Market Knowledge group.

Randy Glein is a Co-Founder & Partner @ DFJ Growth where he looks to partner with entrepreneurs that have achieved market validation and are looking to scale rapidly. Randy's investments include the likes of Twitter, Tumblr, SpaceX and Tesla just to name a few. Prior to DFJ, Randy was CFO @ Feedburner (acq by Google), a business development executive at DIRECTV. Randy was also named to the Forbes Midas List in 2013, 2014, and 2015 as one of the world's top tech investors and to the New York Times / CB Insights list of top 100 venture capital investors in 2016.

In Today’s Episode You Will Learn:

1.) How Randy made his way into VC and came to found DFJ growth?

2.) What does it mean to be a diligent and disciplined investor? How can a futuristic mindset be balanced with an analytical and academic approach to evaluation and due diligence?

3.) How does Randy evaluate invest time horizons? How important is it to push for liquidity events as soon as possible? What is it that LPs really want to see?

4.) How have we seen public market expectations of tech companies change over the last 10 years? What are public market investors willing to give up in exchange for predictability? What are the benefits of tech companies staying private longer?

5.) What are the metrics that suggest a company with market validation and ready to scale into hyper-growth? What are the required levels of revenue and ARR?

Items Mentioned In Today’s Show:

Randy’s Fave Book: Being Digital

Randy's Fave Blog: Brad Feld, Fred Wilson

Randy’s Most Recent Investment: Unity 3D

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

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

Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Intercom.com/20MVC

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.

Jules Maltz, is a General Partner @ Insight Venture Partners (IVP) where he has made investments in the likes of Slack, Zendesk, Twitter, Zenefits and many more incredible companies. Prior to IVP, Jules held roles at the likes of 3i, Admob and Bank of America. Jules has also been named to The Top 40 Under 40 Growth Investors and been featured in the likes of Inc and Fast Company. I also want to say a huge thank you to Rebecca Lynn @ Canvas and Clark Landry for the intros to Jules today.

In Today’s Episode You Will Learn:

1.) How Jules made his way into growth stage investing with IVP?

2.) What are the major trends that Jules has observed in the later stages over the last few years? Where is there funding gaps and room for opportunity? 

3.) What does it take for companies to attain later stage cheques today? What are the benchmarks required? How have we seen these benchmarks change?

4.) What are the fundamental mistakes that CEO's make in these scaling stages? When is the right time to scale rapidly? How does Jules view product market fit?

5.) Jules has previously stated the importance of building the next S curve. What does he mean by this and how should founders adopt this mentality?

Items Mentioned In Today’s Show:

Jules' Fave Book: All The Light We Cannot See

Jules' Fave Blog or Newsletter: Nir and Far

Jules' Most Recent Investment: Checkr

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

Tim Junio is the Co-Founder and CEO @ Qadium, the startup that creates and organizes knowledge about the world's devices. They are backed by some of the best in the business including the likes of Founders Fund (Peter Thiel), NEA (Scott Sandell) and our good friends at Susa Ventures. Prior to Qadium, Tim started his career at the Central Intelligence Agency, and also worked in the Office of the Secretary of Defense, the RAND Corporation, and DARPA. Tim remains a research affiliate at Stanford, where he lectures and advises students on cybersecurity research topics.

In Today’s Episode You Will Learn:

1.) How Tim made his way from the world of the CIA to founding venture backed, Qadium?

2.) How does Tim view his role as CEO? Why does he view leadership and management as 2 different things?

3.) How does Tim view transparency as a leader? What are the conversations that must only be for the founding team? How are those decisions managed and discussed?

4.) Considering Peter Thiel's recent press coverage how does Tim feel about taking 'Thiel Money'? Why does he think Thiel is one of the most interesting and brilliant minds? What are the challenges for Silicon Valley in eschewing the world of politics for the next 4 years?

5.) What does Tim see as the worst of Silicon Valley? What are the benefits to many 'shallow apps' not getting funded? How does this affect startup economics and hiring programmes?

Items Mentioned In Today’s Show:

Tim’s Fave Book: Snowcrash

Tim’s Fave Blog or Newsletter: Bruce Schneier  

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

Ryan McIntyre is a Co-Founder @ Foundry Group, one of the leading VC funds of the last decade with investments in the likes of Fitbit, SendGrid and Makerbot. Prior to Foundry, Ryan started his career in VC at Mobius Venture Capital in January 2000.  While at Mobius Venture Capital, Ryan led the firm’s investments in Postini (acq. GOOG) and Sling Media (acq. DISH). Prior to Mobius, Ryan co-founded Excite in 1993, which went public in 1996 and later became Excite@Home following the $6.7 billion merger of Excite and @Home in 1999. At the time this acquisition was the largest internet transaction to date and created a company that achieved peak revenues of $616 million in 2000.

In Today’s Episode You Will Learn:

1.) How Ryan made his way into the wonderful world of VC and came to co-found Foundry?

2.) At what moment did Ryan realise that he wanted to be a VC rather than his previous life of an entrepreneur? What was the catalyst moment for Ryan?

3.) What does the investment decision making process look like @ Foundry Group? What are the benefits and challenges of implementing such a model?

4.) What are the fundamentals to creating a successful venture partnership? How important is differing skill sets and contrarian thinking?

5.) What makes the great board members to Ryan? How has Ryan seen his style of being a board member alter over the time he has been on boards?

Items Mentioned In Today’s Show:

Ryan’s Fave Book: Dune by Frank Herbert

Investment Ryan Is Most Excited By: Sendgrid

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

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

Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Intercom.com/20MVC

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.

Jason Mendelson is Co-Founder @ Foundry Group, one of the leading VC funds of the past decade with investments in the likes of Fitbit, SendGrid and Makerbot just to name a few. Prior to Foundry Jason co-founded SRS Acquiom, the largest merger and acquisition closing platform that completed over $200Bn in merger transactions. Prior to co-founding SRS, Jason was a Managing Director and General Counsel for Mobius Venture Capital, where he also acted as its chief administrative partner overseeing all operations of the firm. If this was not enough Jason is also the Co-Author, alongside Brad Feld, of the best-selling book, Venture Deals: How To Be Smarter Than Your Lawyer, a must read for all.

In Today’s Episode You Will Learn:

1.) How Jason made his way into the wonderful world of VC having been a lawyer?

2.) Why does Jason believe there is too much BS in VC? What does Jason think causes this opaqueness? How does he look to build a relationship of trust and clarity with his entrepreneurs?

3.) How has the rise of social media affected the transparency and BS element in VC and startups? How can entrepreneurs know when a VC is lying to them? What are the tells?

4.) Jason has previously said that some VC behaviour is 'rather narcissistic'. What does he mean by this? How would he like to see this change in the future?

5.) How does Jason look to optimise board meetings? What are the expectations of both founders and VCs prior to board meetings when it comes to preparation?

Items Mentioned In Today’s Show:

Jason’s Fave Book: Atlas Shrugged

Jason’s Most Recent Investment: Borrowed and Blue

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

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

Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Intercom.com/20MVC

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.

Sarah Guo is an investor @ Greylock Partners, which she joined in 2013. Prior to Greylock, Sarah was at Goldman Sachs, where she invested in Dropbox and helped take Workday public. She advised pre-IPO private technology companies (as well as public clients including Zynga, Netflix and Nvidia) on strategic and financial issues. Previously, Sarah worked with Casa Systems, a venture-funded startup that enables cable operators to meet growing demand for broadband services. She is an advocate for STEM education for women and the underserved, as well as education more generally.

In Today’s Episode You Will Learn:

1.) How Sarah made her way into VC with Greylock Partners?

2.) Question from Josh Elman: What were Sarah's biggest learnings from taking key companies public with GS in 2011? Why is narrative so important? Who has done it well?

3.) How does Sarah view market size and market creation? What is a big enough market size to be attractive? How does this change with time and product?

4.) How does Sarah view the next fundamental platform shift? Where does conversational fit into this thesis? Will we see 'machine learning as a service'?

5.) What does the future of VC look like? What does the next generation of VC need to do to stay on top and ensure pattern matching algorithms do not outperform them?

Items Mentioned In Today’s Show:

Sarah’s Fave Book: The Most Human Human

Sarah’s Most Recent Investment: Rhumbix

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

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

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John Lilly is a Partner at Greylock Partners, one of the world's leading venture funds of the past decade. At Greylock John has led investments in the likes of Instagram (acq by Facebook), Tumblr (acq by Yahoo) and Dropbox. John also sits on the board for Quip, Figma and ClearSlide just to name a few. Prior to Greylock, John was CEO of Mozilla, the organization behind Firefox, used by more than 450 million people. John also co-founded Reactivity, an enterprise security infrastructure company acquired by Cisco in 2007, where he served as founding CEO and later CTO.

In Today’s Episode You Will Learn:

1.) How John made his way into the wonderful world of VC following his time as CEO @ Mozilla?

2.) John has invested in the likes of Quip, Figma and Dropbox, so why are we seeing such a rise in productivity tools beyond Office and Google Apps? Will it always be a market of consolidation like we have seen with the likes of Quip?

3.) Does John believe the first boom of mobile is over? What about sensors makes John excited for the future of the phone? Does John agree with Ben Evans in viewing the phone as the sun of the solar system?

4.) Question from Sarah Guo: How does Greylock to continue to invest in the next big markets, rather than in what has made them successful before? What does the brainstorming sessions and meta-thinking look like internally?

5.) Question from Josh Elman: How does John view growing one's tribe and then growing together through all of your careers? What are the challenges and what is required in order to be successful?

Items Mentioned In Today’s Show:

John’s Fave Book: Thinking Fast and Slow by Daniel Kahneman

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

Harj Taggar is the Founder & CEO @ Triplebyte, the startup that is changing the world of engineering recruitment by building a new kind of interview that evaluates tech skills, not credentials. They have raised from some of our favourite seed investors and all past guests on the show including Felicis Ventures, SV Angel and Initialized Capital. As for Harj, prior to Triplebyte, he was the first partner brought in at Y Combinator since its founding, where he remained as a Partner for 4 years. Before that he was a YC founder, co-founding Auctomatic which was acquired by Livecurrent Media.

In Today’s Episode You Will Learn:

1.) How Harj made his way from the UK to YC's first Partner to now founding Triplebyte?

2.) Question from Garry Tan: What was the most surprising thing when Harj first became a Partner @ YC? What were Harj's biggest learnings from working with Paul Graham and Jessica Livingstone in the early days?

3.) Remaining in those very early stages, from Harj's experience seeing so many companies pass through YC, what do startups look like at those very early stages? How does Harj recommend finding co-founders? Test and iterate on ideas? Work towards product market fit? What does product market fit look like to Harj?

4.) How should we approach hiring as an early stage startup? What are the signs of great hires? What does the optimal interview process look like? How can we optimize the on boarding process?

5.) What should founders look for in VCs and vice versa? What were Harj's learnings on how to be a great seed stage investor from his time with Garry & Alexis @ Initialized??

Items Mentioned In Today’s Show:

Harj’s Fave Book: Surely You're Joking Mr Feynman

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

Rishi Garg is a General Partner @ Mayfield Fund, where he focuses on new media platforms, disruptive financial services and new marketplaces. Prior to joining Mayfield, Rishi was as Vice President of Corporate Development and Strategy at Twitter where he led the company’s most active M&A program, including the acquisitions of Periscope, TellApart, TapCommerce, and many others. Prior to Twitter, Rishi was the first Head of Corporate Development at Square. Rishi was also the Founder of a leading venture-backed startup, FanSnap and has also held roles at Google, Highland Capital Partners and Morgan Stanley.

In Today’s Episode You Will Learn:

1.) How Rishi made his way into VC following time at Twitter and Square?

2.) How does Rishi look to analyse the state of co-founder relationships? What questions get to the core issues? What are the signs that encourage and worry Rishi?

3.) To what extent does a co-founder leaving the company concern Rishi? In what circumstance is this understandable? How should this process be played out?

4.) How much of a role should VCs play post-investment in the relationship of the founders? What are the dangers of this? How should VCs balance helpful and over involved?

5.) Why is Rishi anti the rise of the very large Series? What are the inherent dangers of this? How does he convey this concern to founders?

Items Mentioned In Today’s Show:

Rishi’s Fave Book: The Tibetan Book of Living & Dying, Malcolm X

Rishi's Fave Blog or Newsletter: Wait But Why

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

Tim Chang is a Managing Director @ Mayfield Fund and Tim was referred to me by many other VCs as 'the fittest man in silicon Valley', notable tech publications even write it. His eclecticness does not stop there as he is also a musician in 3 bands and a serious body hacker. As for his investments, he has had AdChina (acquired by Alibaba), Playdom (acquired by Disney) and Basis (acquired by Intel) just to name a few. Prior to Mayfield, he spent time at notable institutions including General Motors and Norwest Venture Partners. It is not only us that appreciate Tim’s skills though as he has also been named to ‘Top 100 Innovators’ on Forbes Midas List for 2 years running.

Maran Nelson is the Co-Founder & CEO @ Clara Labs, the truly human interface that uses conversational intelligence trained on high-quality data to schedule your meetings. They have secured funding from some of the best in the business including previous guest Kent Goldman @ Upside Partnership and Greg Brockman, Founder of the prestigious OpenAI. As for Maran, she is also the Founder of Interact, a community of 100 young makers and technologists coming together for an annual retreat in Tahoe.

In Today’s Episode You Will Learn:

1.) How did Maran come to found one of the hottest AI startups of the day in Clara Labs?

2.) What is the right way to think about a digital assistant? How does Maran think consumer expectations and behaviours will change towards them in the coming years?

3.) Question from Shivon @ Bloomberg Beta: How does Maran think about building an AI company for the long term? How does Clara look to build scalable and transparent feedback loops?

4.) Why is Maran so bullish on the conversational interface? To what situation does this interface lend best? What other verticals and applications could this have in the future?

5.) Does Maran think that humans will always be needed in this process? At what stage will they become obsolete?

Items Mentioned In Today’s Show:

Maran’s Fave Book: East of Eden by John Steinbeck

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

Emily Melton is partner at DFJ, where she focuses on consumer and mobile technology, as well as healthcare technologies and marketplaces. Emily has made investments in the likes of BetterUp, Elation Health, Livongo, Redfin, Shift, and Wellframe. Early in Emily's career, she sourced investments in Box (NYSE: BOX), Meebo (Google), Kudo (Google), RichRelevance, and Flux (MTV Networks). She was also an advisor to Pulse Network (LinkedIn), Healthtap, and Poshmark.

In Today’s Episode You Will Learn:

1.) How Emily made her way into the wonderful world of VC following her meeting with Tim Draper?

2.) How does Emily view the importance of pattern recognition? Why does Emily believe that you should not invest from patterns? What is the difference between a pattern and an investing fad?

3.) Why does Emily hate analogies? Why does she believe it is simplistic thinking? How can this be mitigated for startup founders in describing their company?

4.) How does Emily view the portfolio approach to risk in venture? What questions need to be asked to determine the potential outcome of the business?

5.) Why does Emily get concerned by the rise of the 'celebrity investor'? How can investors build their brand in the proliferated world of early stage startup investing?

Items Mentioned In Today’s Show:

Emily’s Fave Book: Mindset by Carol Dweck, A Theory of Justice by John Rawls

Emily’s Most Recent Investment: BetterUp

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

Josh Stein is Partner @ DFJ where his current board responsibilities include Box (NYSE: BOX), Chartbeat, LaunchDarkly, LendKey, SugarCRM, and previous guests with me on SaaStr in Periscope and Talkdesk. He is also actively involved with the firm's investments in AngelList, Doximity and Twilio (NYSE: TWLO) just to name a few. Prior to joining DFJ, Josh was a VP at Telephia, where he managed a group providing strategic analysis and information to the nation's largest wireless carrier. Previously, Josh was a co-founder for ViaFone (NYSE: SY), a DFJ portfolio company and a leading provider of wireless enterprise applications. Josh met the DFJ team when the firm co-led ViaFone's Series A investment.

In Today’s Episode You Will Learn:

1.) How Josh made his way from the world of operations to Partner @ DFJ?

2.) How does Josh analyze the VC/ Founder fit? How does Josh look to build trust and transparency in that relationship? What is an example of how Josh has changed his style to fit the character of an entrepreneur?

3.) Question from Greg Sands: What did Josh see in the early days of Box with a young Aaron Levie, what was it that made him so excited?

4.) Question from Mamoon Hamid @ Social Capital: Looking at Box today, what will it take for Box to 10x their value? What needs to happen in the market? What needs to happen to the product roadmap?

5.) Question from Jason Lemkin @ SaaStr: How is it that we are seeing companies like TalkDesk and Twilio grow at a rate never seen before in today's SaaS environment?

Items Mentioned In Today’s Show:

Josh’s Fave Blog: TermSheet

Josh’s Fave Book: Insanely Simple: The Obsession That Drives Apple's Success

Josh’s Most Recent Investment: LaunchDarkly

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

Henry Ward is the Founder & CEO @ eShares, the No 1 cap table management platform providing equity management, 409A valuations and liquidity all in one place. They are backed by leading investors and past guests including USV, SV Angel, Spark Capital, Semil Shah, Manu Kumar, Tim Draper and Kamal Ravikant, just to name a few. Prior to eShares, Henry was Founder @ SecondSight, the first registered investment advisor to go direct to your brokerage and improve your portfolio.

In Today’s Episode You Will Learn:

1.) How Henry made his way into the world of startups and came to found eShares?

2.) How does Henry challenge the notion that investors should have such high fail rates? How does Henry believe investors can build a strong and sustainable portfolio without home runs?

3.) Why does Henry believe that investors will never accept market risk? How much of a role does Henry believe herd mentality plays in the VC ecosystem?

4.) How does Henry view the increasing exit horizons for startups? Is this a problem? How can we create liquidity options pre large exits?

5.) How does Henry view the role of regulation in private markets? How does this differ to public markets? What would Henry like to see change in the VC ecosystem?

Items Mentioned In Today’s Show:

Henry’s Fave Blog: Hacker News

Henry’s Fave Book: The Essays Of Warren Buffett

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

Phil Libin is Managing Director @ General Catalyst and Founder and Executive Chairman @ Evernote. At Evernote, Phil took the company from idea generation to productivity powerhouse allowing millions of users around the world to remember everything and in the meantime, providing Evernote with over $160m in VC funding from some of the very best including Sequoia Capital. Now in the world of VC, Phil has a particularly fondness towards all things bots, a theme we discuss heavily today. Phil has also made several angel investments in the likes of Gusto, TellApart and Binary Thumb just to name a few.

In Today’s Episode You Will Learn:

1.) How Phil made his way from Founder @ Evernote to Managing Director @ General Catalyst?

2.) Niko Bonatsos, Managing Director @ General Catalyst asks: What were your biggest takeaways from your time with Evernote that lend to you being a better investor? What are the biggest surprises about the move into VC?

3.) Why have we seen an explosion of hype and excitement around the bot space over the past year? What was the catalyst for the rise of the bot?

4.) Why are we not there yet with bots? Should all be conversational? How does the infancy of messaging platforms affect the rise of bots? What unsolved technical challenges remain?

5.) Will the transition to bots and conversational interfaces represent a major point of disruption or more of an evolution in the interface paradigm?

Items Mentioned In Today’s Show:

Phil’s Fave Blog: The Economist

Phil’s Fave Book: The Three Body Problem

Phil’s Most Recent Investment: Sunflower Labs

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