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.

The Simba Hybrid. The most advanced mattress in the world. With a unique combination of two thousand five hundred conical pocket springs and responsive memory foam, it offers the perfect support for two people. A mattress that responds to you and your partner’s sleeping patterns. Delivered free, with a one hundred night sleep trial, free returns and a ten year guarantee. Start your free trial at simbasleep.com

Cirrus Insight is a plugin for sales pros who use Gmail and Outlook.  It automatically updates activities in Salesforce so you don’t have to.  It was named #41 on the Inc. 500 list of fastest-growing companies, and it has more than 1,700 customer reviews on the Salesforce AppExchange. Today, it serves over 150,000 sales people across 5,000 organizations using Gmail, Outlook, iPhone, iPad, and Android. Cirrus Insight is perfect for sales, support, and success teams who want to save time, schedule 3x more appointments, track email opens and much more with Salesforce information at their fingertips in the inbox. www.cirrusinsight.com/20VC

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!

Charlie O’Donnell is the Founder and Sole Partner @ Brooklyn Bridge Ventures, the first venture capital fund based in Brooklyn, who manage $23m across 2 funds. Prior to founding Brooklyn Bridge, Charlie worked at the prestigious First Round Capital, with the likes of Josh Koppelman and Union Square Ventures with Fred Wilson. If that wasn’t enough Charlie is one of only a dozen to be named to Business Insider’s 100 Most Influential People in NY Tech five or more times and has served on the founding board of the New York Tech Meetup and is one of the group’s first 100 members. His blog, This is Going to Be BIG!, is one of the ten most widely read VC blogs in the country with over 8,000 readers.

In Today’s Episode You Will Learn:

1.) How Charlie made his move from college to venture and then struck out on his own from USV?

2.) Charlie has previously said that 'venture capital is humbling'. How does Charlie look to construct his portfolio with Brooklyn Bridge? How does he come to terms with the fact he will be wrong most of the time?

3.) What are Charlie's views towards follow-on funding and allocating reserves of the fund? How important is this from a return multiple perspective? How much of a difference does it make for founders to raise a next round with 100% of seed investors committed?

4.) Charlie has previously suggested the importance of being helpful and hard working. Is that really enough to build a brand in today's competitive VC environment? Is brand a form of defensible IP?

5.) How does Charlie react to Ben Lerer's suggestion that Jet.com and Dollar Shave Club are the first dominoes of an incoming wave of e-commerce M&A?

Items Mentioned In Today’s Show:

Charlie’s Fave Blog: Wait But Why

Charlie's Most Recent Investment: Industrial Organic

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

Nitesh Banta is the Founder and CEO @ B12, the startup that uses AI to superpower their team of world class creatives to create even more intelligent websites. They have backing from the likes of Jim Breyer, General Catalyst and our friends at Founder Collective. As for Nitesh, prior to B12, he was on the dark side as a VC with General Catalyst for 5 years before Co-Founding Rough Draft Ventures, the General Catalyst program designed to develop the next generation of student founders.

In Today’s Episode You Will Learn:

1.) How Nitesh made the move from VC with General Catalyst to AI Startup founder with B12?

2.) How difficult was it for Nitesh to leave the security of venture to start B12 as Founder? What does Nitesh suggest to those that are unsure of whether to make the jump?

3.) Why does Nitesh believe that AGI (artificial general intelligence) is not as close as people predict? What are the implications of this towards humans relationship with technology?

4.) Is Nitesh bullish on humans creating new and unique machine learning algorithms or the rise of 'machine learning as a service as a sector? Where does the real value lie, the data or the machine learning algorithms?

5.) Why is Nitesh contra the common pessimism surrounding AI and the future of work? How does Nitesh believe AI will impact human work processes in a positive way?

Items Mentioned In Today’s Show:

Nitesh’s Fave Blog: Bill Gurley: Above The Crowd, Nuzzel

Nitesh’s Fave Book: Oh The Places You'll Go

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

Kent Goldman is the Founder of Upside Partnership, one of the leading seed-stage investment firms in SF with investments in the likes of Laurel and Wolf, Digit and Lily. In 2015, he was named to the Midas Brink List. Prior to forming Upside Partnership in 2014, Kent was a Partner at seed investment pioneer First Round Capital. While there he led investments in companies including Airware, Hotel Tonight, and MemSQL. He also served on the board of Mashery (acquired by Intel). Earlier in his career, Kent was a member of Yahoo!’s corporate development team and also led business strategy for Yahoo! products generating $1 billion in annual revenue.

In Today’s Episode You Will Learn:

1.) How Kent made his way into the world of early stage investing and came to found Upside?

2.) What were the big takeaways from First Round for Kent? How has he applied those learnings to his formation of Upside?

3.) What does Kent look for in the LPs that invest in his fund? Why should founders look to learn which LPs are invested in the fund investing in them?

4.) How has Kent seen his investment decision-making process alter with time? What have been the big changes?

5.) Why does Kent believe valuation does not matter so much at the seed stage? What does really matter to him at the seed stage? How does this progress with rounds?

Items Mentioned In Today’s Show:

Kent’s Fave Blog: Howards Marks: Oaktree Capital

Kent’s Fave Book: A River Runs Through It And Other Stories

Kent’s Most Recent Investment: Live Neighborly

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

David Politis is the Founder & CEO @ Bettercloud, the first ever unified SaaS management platform. Bettercloud have raised over $40m in funding from some of today's best investors including past guests from Accel, Greycroft Partners and Flybridge Partners, just to name a few. Before founding BetterCloud, David was an early employee of Cloud Sherpas (acquired by Accenture [NYSE: ACN]) where David led Cloud Sherpas to become the leading Google Apps services provider and reseller to SMBs worldwide. Prior to Cloud Sherpas, David was the founding employee and General Manager of Vocalocity (acquired by Vonage [NYSE: VG]), which he grew into one of the top providers of cloud PBX technology.

In Today’s Episode You Will Learn:

1.) How Dave came to found Bettercloud? What was the a-ha moment for him?

2.) Why does David like to invest in everything but perks? What are the challenges of incentivising a team with Perks? What are the alternatives?

3.) What are the limits to transparency? Can there ever be too much transparency? How do you engender a culture of radical transparency within the workforce? 

4.) How was the fundraising process for David? how did it alter and develop with every round? What did he do well and what would he improve upon?

5.) How can founders optimise the on boarding process for new hires? What is fundamental? What are the common mistakes and how can this be hacked for success?

Items Mentioned In Today’s Show:

David's Fave Blog: Recode

David's Fave Book: Banker To The Poor 

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

Parker Thompson is a Partner @ AngelList and creator of popular parody Twitter Account, Startup L Jackson. At AngelList Parker has made investments in the likes of former guests, Algolia, Realty Shares and Keen IO. Prior to joining AngelList, Parker was a Partner at 500 Startups in SF and his illustrious path prior to investing includes Pivotal Labs, co-founding PlaceSite, preserving the interwebs at the Internet Archive, and working on digital copyright at UC Berkeley’s iSchool.

In Today’s Episode You Will Learn:

1.) How Parker made his way into the world of early stage investing from the world of operations?

2.) How does Parker look to evaluate startup founders? What questions does he like to ask? What traits does he like to see in the core exec?

3.) Why does Parker think "not enough traction" is a BS VC excuse? How should VC's approach saying no to founders? What are the real reasons a VC is saying no in this case?

4.) Why does Parker believe the jump to Series A is bigger than ever? What has caused this? What metrics do startups have to achieve to make this move successfully?

5.) How should founders determine how much money to raise? If they can should they raise a 'warchest'? Why should founders not be concerned with dilution in the early days?

Items Mentioned In Today’s Show:

Parker’s Fave Blog: Stratechery, Nuzzel

Parker’s Fave Book: The Modernist Cuisine 

Parker’s Most Recent Investment: Common Networks 

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

Rebecca Lynn is a Partner @ Canvas, where she focusses on Fintech, Digital Health, SaaS and mobile. Rebecca led an early stage investment in Lending Club, which was the largest US technology IPO of 2014 and the 4th largest Internet IPO since 2001. She has also led investments in the likes of Check (acquired by Intuit), RelateIQ (acquired by Salesforce), Proximity, Practice Fusion and more incredible companies. Prior to being in VC, Rebecca held operational roles at NextCard where she rose to become VP of Marketing and Head of Customer Acquisition and saw the company going public with a $1.3bn market cap.

In Today’s Episode You Will Learn:

1.) How Rebecca made her way into the wonderful world of VC?

2.) How does Rebecca view the importance of brand and thematic focus in the world of VC today? How can a VC be focussed thematically without missing moonshots?

3.) What were Rebecca's biggest lessons from sitting on boards with the likes of Mary Meeker and Larry Summers? How did that change how Rebecca viewed being a board member?

4.) "Fintech is all about distribution and acquisition". What does Rebecca make of this statement? How have we seen evolution in both distribution and acquisition in the rising tide of new fintech startups?

5.) How does Rebecca analyse fund economics? What does she make of the mega $1Bn funds raised over the last year? What is the optimal size fund for Rebecca?

Items Mentioned In Today’s Show:

Rebecca’s Fave Blog: The Daily Shot

Rebecca’s Fave Book: Influence by Robert Cialdini

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

Ryan Smith is the Founder & CEO @ Qualtrics, an online survey company with 1,200 employees and a valuation of more than $1bn. They have backing from some of the world’s best investors including the likes of Sequoia, Accel and Insight Venture Partners having raised a $150m Series B in 2014. As for Ryan, there are many awesome things, first, he has built Qualtrics from Utah allowing him to gain perspective outside of the traditional tech bubbles, second, he held off on attain VC funding for many years despite the common belief that it is necessary for unicorn growth and finally he has the most incredible work life balance I have seen and if you have not already you must check out this piece on him in Forbes, it really is a must.

In Today’s Episode You Will Learn:

1.) How Ryan made his way into startups and came to found Qualtrics?

2.) Sequoia’s Bryan Schreier states that Ryan’s success is due to running the company on ‘first business principles’. What does he mean by this? How does this affect the way Ryan runs Qualtrics?

3.) Why did Ryan decide to bootstrap the company for such a long time with the likes of Accel and Sequoia looking to invest? What are the benefits of retaining such control? What are the financial requirements to do so?

4.) What makes the best CEO’s? How do they view the internal structure of the company? How do they perceive their role? How do they manage their day and optimise their time?

5.) How does Ryan look to instill ‘radical transparency’ in the organisation? What are the benefits of doing so? Can an organisation ever be too transparent? What are the challenges of such transparency?

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.

Pearl believes the latest automotive technology should be available to every driver – whether it’s time for you to buy a new car or not. RearVision is our first step in driving this commitment forward. Pearl RearVision is the only wireless backup camera and alert system that installs in minutes and updates throughout its lifetime. Pearl literally takes less than 10minutes to install and is completely wireless because it’s solar powered. Since RearVision is software based, we’re able to push updates and new features over the Pearl App in the exact same way you receive updates for other apps on your phone. Pearl RearVision is perfect for anyone who wants to upgrade their car in minutes. Pearl RearVision is $499.99 and available at PearlAuto.com. It’s also available on Amazon and through Crutchfield.

Xero is beautiful, easy-to- use online accounting software for small businesses. With Xero, you can easily manage your accounting anytime, anywhere from your computer or mobile device.When you add Xero to your small business you are able to: Send online invoices and get paid faster. Get an instant view of your cash flow. Track your payroll and keep tabs on your inventory. Partner with your accountant and bookkeeper in real time whenever you like. You can also customize your Xero experience with over five hundred business apps, including advanced solutions for point-of- sale, time tracking, ecommerce and more. Sign up for a free thirty-day trial at xero.com/20vc

Garry Tan is a Co-Founder and Managing Partner @ Initialized Capital, one of Silicon Valleys leading early stage seed funds. Prior to founding Initialized, Garry was a Partner at Y Combinator where he invested in and directly worked with over 700 companies in 5 years from the earliest possible stage, often just an idea. Garry's portfolio includes the likes of previous guests Tilt, Eero, Flexport, LendUp and many more incredible companies.
Before being at YC, Garry Co-Founded Posterous and helped build it to a world-class website used by millions, ultimately acquired by Twitter. Garry also co-founded the engineering team for Palantir Technology's quant finance analysis platform.

In Today’s Episode You Will Learn:

1.) How Garry made the transition from Founder @ PostHaven to YC Partner to Initialized GP?

2.) What were Garry's biggest takeaways from advising 700 startups at YC that he has taken with him to Initialized?

3.) Why does Garry believe now is the golden age for early stage investing? What opportunity does the mass of late stage capital provide the early stage?

4.) How does Garry approach desired ownership? What level of ownership provides incentive for a VC to work whilst also allowing collaboration with other VCs in a round?

5.) What are Garry's thoughts on the rise of thematic investing? Why does he not believe it to be optimal at the seed stage?

Items Mentioned In Today’s Show:

Garry’s Fave Blog: SaaStr

Garry’s Fave Book: Chaos Monkeys

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