20VC: Why Fundraising Is Like Dating and How to Play The Game Successfully & How To Increase The Flexibility of Your Burn When Growth is Ambiguous with Rachel Blumenthal, Founder & CEO @ Rockets of Awesome

Eric Vishria is a General Partner @ Benchmark, one of the world's leading VC funds with a portfolio including the likes of Twitter, Uber, Snapchat, eBay, WeWork, Yelp and many more revolutionary companies of the last decade. At Benchmark, Eric has led deals and sits on the board of the likes of Confluent, Amplitude, and Bugsnag. Prior to being in VC, Eric was the Founder & CEO @ Rockmelt, the startup that sought to re-imagine the browser for the way people use the web today, the company was ultimately acquired by Yahoo in 2013. Prior to Rockmelt Eric held numerous different roles including VP of Products @ HP and VP of Marketing @ Opsware. In Today's Episode You Will Learn: 1.) How Eric came to be one of the 5 GP's at Benchmark following operational success with Rockmelt, HP and Opsware? 2.) Why does Eric believe the pendulum has swung too far to the operational route into VC? What are the under-appreciated benefits of career VCs and the perspective they bring? How does Eric expect the pendulum to swing in the coming years? 3.) What makes the best-performing venture partnerships? How does Benchmark think about partner composition and career pre-VC? How does Benchmark structure investment decision-making? Why do they favor advocacy over unanimity? 4.) What does Eric mean when he says we are at the beginning of an infrastructure renaissance? What opportunities does this create in the venture landscape? How does this lead Eric to consider the current state of the consumer landscape? 5.) How does Eric view multi-stage investing? Why does Eric and Benchmark favour stage specifity when it comes to investing? What are the dangers of larger stage funds investing in earlier rounds for optionality? Items Mentioned In Today's Show: Eric's Fave Book: Endurance: Shackleton's Incredible Voyage To The Antarctic Eric's Most Recent Investment: Confluent As always you can follow Harry, The Twenty Minute VC and Eric on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic's resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world's best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

25 Sep 201724min

Mario Schlosser is the Founder & CEO @ Oscar, the startup that makes health insurance easy. They have raised over $700m in funding from some of the world's best investors including the likes of Founders Fund, Google Capital, Thrive Capital, Lakestar, Khosla Ventures and Jim Breyer just to name a few. Previously, Mario co-founded the largest social gaming company in Latin America and held roles with the likes of Bridgewater Associates and McKinsey. Fun fact, as a visiting scholar at Stanford University, Mario wrote 10 computer science publications, including one of the most-cited computer science papers published in the past decade. In Today's Episode You Will Learn: 1.) How Mario made his way into the world of healthcare and Oscar from founding Latin America's largest social gaming company? 2.) Why is insurance one of the most complex spaces in tech? Why is there a chance for companies, not governments, to cut costs and innovate on the current system? Does Mario agree with Brian Singerman, "once we go to a single player, innovation ends", thesis? 3.) Oscar has raised over $700m, to what extent does Mario believe that too high a valuation can be a liability? How did Mario look to select his investors? What are the challenges of raising funds for a category-defining opportunity? 4.) Oscar now has over 600 in the team, where have been the inflection points in the scaling of the company? Where have things broken? How does Mario look to rectify and observe these inflection points ahead of time? 5.) How does Mario look to optimise team composition? How does he look to balance athletes with heavy domain experts? Does Mario believe that too much domain expertise can prevent innovation due to a lack of naivety? Items Mentioned In Today's Show: Mario's Fave Book: Herr Lehmann Mario's Fave Blog: Spiegel As always you can follow Harry, The Twenty Minute VC and Mario on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic's resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world's best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

22 Sep 201727min

Jeremy Conrad is a Partner @ Lemnos Labs, the fund that believes in the earliest stages of building hardware, every dollar counts, every hour matters and every decision is crucial to success or failure. Consequently, Lemnos invests in pre-seed and seed hardware startups encountering these very real challenges. Among their portfolio is the likes of previous guest Swift Navigation and Airware, just to name a few. As for Jeremy, prior to VC he was in the United States Airforce where he was in charge of an $80m tests and targets group and was also responsible for the BMC4I system of the Airborne Laser (ABL). In Today's Episode You Will Learn: 1.) How Jeremy made his way from the United States Airforce to investing in the next generation of great hardware founders with Lemnos? 2.) Why does Jeremy believe that now is the time for robotics? What megatrends mean now is the right time? Why does Jeremy believe that core AI today is largely a bunch of nifty tricks? 3.) Why does Jeremy believe that Silicon Valley will dominate the future of robotics? What characteristics does the valley have that mean this is the case? What is the dirty secret of Silicon Valley? 4.) How does Jeremy view the funding environments for hardware? Where is there constrictions of capital for hardware startups? What must hardware founders have in place in order to raise a Series B? 5.) Why does Jeremy believe that consumer electronics is the hardest space for venture today? With the likes of Juicero and Pearl, is consumer still possible today? Are the likes of GoPro and FitBit merely anomalies in the dataset? Items Mentioned In Today's Show: Jeremy's Fave Book: The Better Angels of Our Nature Jeremy's Fave Blog: Dan Primack: Pro Rata Jeremy's Most Recent Investment: Marble As always you can follow Harry, The Twenty Minute VC and Jeremy on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic's resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world's best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

20 Sep 201724min

Mike Volpi is a General Partner @ Index Ventures, one of the world's leading venture funds with a portfolio including the likes of Facebook, Dropbox, Slack, Supercell and Deliveroo just to name a few. Mike currently sits on the boards of prior guests, Cockroach Labs and Wealthfront, as well as Blue Bottle Coffee, Sonos and Zuora just to name a few. Prior to Index, Mike was a director @ Cloud.com (acq by Citrix) and StorSimple (acq by Microsoft). Before that, Mike held a number of executive positions including Chief Strategy Officer at Cisco. He also serves on the board of Fiat Chrysler Automotive. In Today's Episode You Will Learn: 1.) How Mike made his transition from operator and M&A exec to General Partner @ Index and opening their West Coast Office? 2.) Question from Dave Morin @ Slow: How did Mike's childhood in Italy and Japan affect how he views and interacts with entrepreneurs today? Question from Danny Rimer: How has Mike found the transition from player to coach with the move to VC? 3.) Question from Andy Rachleff: Having seen both the US and European venture markets, how do they compare? Why does Mike think being an entrepreneur in Europe is far more solitary? What does it take to create a VC brand, like Index in an already very crowded West Coast market? 4.) Having had a front-row seat for the brand building of the likes of Sonos, Blue Bottle and Eero, what does Mike believe are the core tenets to building generation-defining brands? How has this changed over the last 5-10 years? 5.) Does Mike agree with Rob Siegel that the enterprise market is now less exciting given we might be entering a period of consolidation? Why does Mike believe this actually represents opportunity? How will we see open source play a role in the next wave of these enterprise companies? Items Mentioned In Today's Show: Mike's Fave Book: Undaunted Courage Mike's Fave Blog: The Information Mike's Most Recent Investment: Eero As always you can follow Harry, The Twenty Minute VC and Mike on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic's resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world's best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

18 Sep 201729min

Charlie Lee is the creator of Litecoin, the most popular alternative currency to Bitcoin, which Charlie created as a side project in 2011 while working at Google. Today Litecoin has a market cap of $3.29Bn. As well as creating Litecoin, Charlie is also the Director of Engineering @ Coinbase, working alongside recent 20VC guest and Coinbase founder, Brian Armstrong. Prior to this, Charlie held roles at Microsoft, Google and Guidewire. In Today's Episode You Will Learn: 1.) How Charlie made his way from Google to Coinbase to founding Litecoin in his free time? What were Charlie's biggest takeaways from being at Coinbase? 2.) What does Charlie believe is the biggest barrier to the world of cryptocurrency and BTC? What is the holy grail to securing this and the future of the space within mass consumer usage? 3.) How does Charlie think about the largest problem for crypto and BTC, scaling? Why does Charlie believe that Ethereum will have large problems scaling? How does Charlie assess the balance of centralization, scaling and transaction efficiency? 4.) Why is Charlie's biggest concern the current ICO market? Why does he believe it is the "wild west"? What happens to alternative currencies when the ICO market crashes? Who are the ultimate winners in the ICO markets? 5.) How does Charlie analyse the differing communities when comparing ETH to BTC to LTC? Does community serve as a core form of IP for currencies and their stability moving forward? Items Mentioned In Today's Show: Charlie's Fave Book: Game of Thrones As always you can follow Harry, The Twenty Minute VC and Charlie on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic's resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world's best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

15 Sep 201722min

Kathleen Utecht is a General Partner @ Core Innovation Capital, I would say one of the most under the radar but immensely exciting funds in market and they are looking to revolutionize financial services with their portfolio. With their portfolio are the likes of NerdWallet, PayJoy, fundera and Mayvenn just to name a few. Prior to Core, Kat was an investor at Comcast Ventures and WVP Ventures. Prior to her venture roles, Kath invested in and led Green Rock Entertainment, an online/offline commerce startup. Before that, Kat cut her teeth in the world of finance working as an investment banker at Raymond James. In Today's Episode You Will Learn: 1.) How Kat made her way from car entrepreneur dreams to operator to now, General Partner @ Core? 2.) Why does Kat believe that "society is on a downgrade"? Does Kat agree with the Thiel thesis of "we expected flying cars and were given 140 characters"? Where does Kat most want to see entrepreneurs spending their time and skills? 3.) How does Kat view regulation with regards to startup operations and expansion? Why does Kat believe that "sector specific funds should be in every highly regulated deal"? What are the core benefits? How can VCs really aid with regulation? 4.) Kat has previously said that "VC is a lifestyle not a job", what does Kat mean by this? How does this mean VCs should behave with regards to founder interactions and communications? How can entrepreneurs stress test whether a VC has this belief? 5.) How does Kat view the process of losing companies? What does her post mortem analysis look like? Why does Kat believe that if you do not lose companies, you are not taking enough risk? Items Mentioned In Today's Show: Kat's Fave Book: Atlas Shrugged Kat's Fave Blog: AVC by Fred Wilson As always you can follow Harry, The Twenty Minute VC and Kat on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic's resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world's best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

13 Sep 201727min

Andy Weissman is a Partner @ Union Square Ventures, one of the world's leading VC firms with investments in Twitter, Twilio, Zynga, Soundcloud, Tumblr, Lending Club and many more. At USV, Andy sits on the boards of YouNow, ScienceExchange, Figure 1 and previous guest, CircleUp. Prior to joining USV, in 2007 he co-founded betaworks, which both created and invested in social, real-time applications and services. You can also check out Andy's fantastic blog here. In Today's Episode You Will Learn: 1.) How Andy made his way into the world of startups and investing, came to found Betaworks and then made the move to USV? 2.) Andy has previously said the business "is more about luck than skill and process rather than foresight". Why does Andy place so much emphasis on process? How has Andy seen his process evolve over the years? How does the process of an individual balance with the process of the firm? 3.) Why does USV not agree with voting as a method of investment decision making? How do Andy and USV approach reserve allocation? What model and simulators do they use to determine which companies receive follow on funding? 4.) Why does Andy believe that recycling cash from early exits is good for everyone? How has Andy found that LPs respond to this? What is the balance? What is the right amount for recycling, 110%, 120% or 130%? 5.) How does Andy view price sensitivity? To what extent does Andy agree with Peter Fenton that "valuation is a mental trap"? Has there been a time when Andy has lost a deal due to price? How has that changed his psyche and approach to the topic? Items Mentioned In Today's Show: Andy's Fave Book: On The Road by Jack Kerouac Andy's Fave Blog: Phish.net, Continuations, Radio Free Mobile Andy's Most Recent Investment: Flip As always you can follow Harry, The Twenty Minute VC and Andy on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic's resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world's best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

11 Sep 201729min

Wayne Chang is a serial entrepreneur and angel investor. His latest company, Crashlytics, was acquired by Twitter in a 9-figure acquisition, its largest acquisition at the time. 5 years later, Crashlytics was acquired again, this time by Google. Wayne is also a prolific angel investor with a portfolio that includes the likes of OpenDoor, SoFi, Gusto, JetSmarter and Planet Labs just to name a few. If that was not enough, Wayne is also a limited partner in several prominent funds including the likes of 137 Ventures, Baseline Ventures, and Boston Seed Capital. In Today's Episode You Will Learn: 1.) How did Wayne make his way into the world of founding tech companies and what was the founding story with Crashlytics? 2.) Why does Wayne believe that one of the first hires founders must make is a recruiter? What are the benefits of having this as a dedicated function so early? What must founders look for in these early recruiter hires? 3.) Why does Wayne believe that with regards to VC, you "must avoid the board room"? What is a better environment to interact and pitch? How can early stage startups look to stand out in the rather process driven pitching game? 4.) What is the optimal way for founders to be put in touch with VCs? Should founders speak to associates in the fundraising days? Why does Wayne believe the power of the warm intro is lopsided? 5.) How can founders look to create a sense of urgency within the VC community when raising and closing their round? How can founders look to create a sense of FOMO within the investor class they are pitching? Should they name other funds they are seeing? Items Mentioned In Today's Show: Wayne's Fave Book: Enders Game Wayne's Fave Blog: Hacker News As always you can follow Harry, The Twenty Minute VC and Wayne on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. Pendo delivers the only complete platform that helps companies create great products. The Pendo Product Experience Platform enables product teams to understand product usage, collect user feedback, measure NPS, assist users, and promote new features in-app – all without requiring any engineering resources. This unique combination of capabilities helps companies improve customer satisfaction, reduce churn, and increase revenue. Pendo is the proven choice of Salesforce, Cisco, Optimizely Citrix, BMC and many more leading companies. Start a free trial at http://go.pendo.io/harry Treehouse is an online school where you can learn how to build websites and apps. Their course library has thousands of hours of content, where you can learn all sorts of topics, including Javascript, iOS, Android and more. With high-quality video instruction from real industry experts teaching you all you need to know, and quizzes and code challenges keep you engaged and on track. Learn on your own schedule and go from beginner to pro. Go to teamtreehouse.com to start your free trial.

8 Sep 201732min