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The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

The Twenty Minute VC takes you inside the world of Venture Capital, Startup Funding and The Pitch. Join our host, Harry Stebbings and discover how you can attain funding for your business by listening to what the most prominent investors are directly looking for in startups, providing easily actionable tips and tricks that can be put in place to increase your chances of getting funded. Although, you may not want to raise funding for a startup. The Twenty Minute VC also provides an instructional guide as to what it takes to get employed in the Venture Capital industry, with VCs giving specific advice on how to get noticed from the crowd and increasing your chances of employment. If that wasn't enough our amazing Venture Capitalists also provide their analysis of the current technology market, providing advice and suggestions on the latest investing trends and predictions. Join us so you can see how you can get BIG, powerful improvements, fast. Would you like to see more of The Twenty Minute VC, head on over to www.thetwentyminutevc.com for more information on the podcast, show notes, resources and a more detailed analysis of the technology and Venture Capital industry.
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May 24, 2019

Mathilde Collin is the Co-Founder & CEO @ Frontreinventing the email inbox with new workflows and efficient collaboration so people can accomplish more together. To date, Mathilde has raised over $79m in VC funding with Front from some of the best in the business including Bryan Schreier @ Sequoia, Initialized, Uncork Capital, Boldstart and individuals including Andrew Chen, Elad Gil, Ray Tonsing the list goes on. With 4,500+ customers, and 100+ employees, in Paris, San Francisco and Amsterdam, Front is one of the fastest growing companies in SaaS and Mathilde has become a thought leader for the next generation of SaaS CEOs, read more on her blog here. 

In Today’s Episode You Will Learn:

1.) How Mathilde made her way from product manager in Paris to founding one of the hottest and fastest growing companies in the world of SaaS in the form of Front?

2.) What does Mathilde mean when she says, "I would choose discipline over vision any day of the week"? What does discipline really mean to Mathilde? Why is it a priority in the early days? How can a VC stress test and determine the level of discipline a founder has in first meetings? What are the signs or leading indicators?

3.) Communications:

  • Investor Updates: What is Mathilde's biggest advice to founders when it comes to investor updates? What should they contain? How often should they go out? How should founders ask for help in updates? Where do founders often make mistakes?
  • Revenue Updates: Why does Mathilde do revenue updates with the team? Is there a danger of being too transparent? What are the benefits of this transparency? What is the structure of the update? Who is privy to it?
  • Direct Reports: How does Mathilde communicate with her direct reports? Why does Mathilde believe that CEOs should have their calendar public? What is the right cadence for these direct reports?

4.) How does Mathilde approach and think about fundraises with Front today? How can founders know when is the right time to raise? How does Mathilde think about building relationships with investors when she is not raising? How transparent should founders be when they are not raising? What are Mathilde tips for always overshooting her numbers? How does Mathilde conduct DD on potential investors in the company?

Items Mentioned In Today’s Show:

Mathilde’s Fave Book: The Power of Now: A Guide to Spiritual Enlightenment

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

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

May 20, 2019

Jeff Housenbold is a Managing Partner @ Softbank Vision Fund, the leading and most influential firm in the venture space investing more than $93 billion in the businesses and technologies they believe will enable the next stage of the information revolution. To date, Jeff has backed the likes of OpenDoor, DoorDash, Wag, Clutter, Brandless and Katerra just to name a few. Prior to Softbank, Jeff spent 11 years as President and CEO @ Shutterfly, during his tenure the company enjoyed incredible growth with the growth of the team from 103 to 2,600 employees. In the past, Jeff has sat on the board of Caesers Entertainment (the world's largest casino entertainment company), Groupon and Chegg and is currently a member of the Board of Trustees of Carnegie Mellon University.

In Today’s Episode You Will Learn:

1.) How Jeff made his way from being President and CEO of Shutterfly for 11 years to writing $200m-2Bn checks as Managing Partner @ Softbank Vision Fund?

2.) We have Wag on the small end and Uber on the high end, so how does Softbank think about portfolio construction and insertion point today? Blended, at what stage would Softbank like their capital to be most concentrated? Does Jeff believe that ownership is largely built on the first check or built over time?

3.) What does the internal investment-decision making process look like for Softbank? How does this decision-making process change when considering reserve allocation? How does Softbank think about and approach reserves given their later entry into companies? Given the size of check being written, what does diligence look like in the standard process for Softbank?

4.) Given the forthy pricing environment today, how does Jeff assess his own price sensitivity? Does this differ depending on the stage of entry? With many suggesting Softbank have extended the period of privatisation for companies, how does Jeff and the team think about liquidity? How does Jeff think about the future of secondaries for seed managers and angels?

5.) Question from Eric Wu @ Opendoor: How does Jeff think about and analyse the opportunity in fragmented categories? What is the bottoms up thought process to this thesis? Speaking of Opendoor, how does Jeff most like to work with the founders he backs? How does Jeff think about he allocates his time across the portfolio?

Items Mentioned In Today’s Show:

Jeff’s Fave Book: The Fountainhead

Jeff’s Most Recent Investment: Katerra

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

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

Want to book your own travel and not have the admin team chasing you for every receipt? Take your business travel program to the next level with TravelPerk. They’ve built the world’s largest inventory of low-cost flights, hotels, airbnb, trains, cars, you name it, all in one gorgeous booking experience. AND they’re built for business. Book, manage, support, analyze, and optimize your business travel, all in one place. Add to this a support team made up of dedicated travel experts who deliver a 7-star experience around the clock, and you’re taking corporate travel out of the dark ages. 20VC listeners can score a free lounge pass to over 1200 airports for a whole year. Not only will you be able to add “company savior” to your email signature, but you can also enjoy the luxury of amazing airport lounges all over the world. Click here to find out more!

May 17, 2019

Jon Dishotsky is the Founder & CEO @ Starcity, the startup on a mission to make cities more affordable to everyone allowing you to live with great people in the city you love. To date, Jon has raised over $28m in funding for Starcity from the likes of Social Capital, Y Combinator, Bullpen Capital, NEA and Kima Ventures in Paris, just to name a few. Prior to founding Starcity, Jon did over 3M square feet of commercial real estate transactions for clients including Optimizely, Cruise Automation, Weebly, Zenefits and many more. Before that he spent 8 years at the prestigious Cushman & Wakefield. Jon is also an active angel investor with investments in the likes of Remote, Fond and Savvy.

In Today’s Episode You Will Learn:

1.) How Jon made his way from doing real estate transactions for clients including YC to being one of the hottest prop tech startups making cities affordable with Starcity?

2.) Why did it take so long for the venture ecosystem to get excited by the rise of proptech? What was the catalyst? When advising VCs, how do you advise them to get comfortable investing in these heavy asset, non-lean startup businesses? What are the biggest mistakes investors make when analysing proptech?

3.) What were some of Jon's biggest takeaways from his time at YC? How does Jon advise other founders looking to get into YC today? When it comes to investor selection, in what cases would Jon take a lower valuation against other offers? How does Jon advise founders on investor selection? What questions should they ask? Why is it like hiring? What are the common mistakes that Jon sees founders make when selecting investors?

4.) How does Jon advise founders when it comes to improving the quality of their mental health? Where do Jon struggle? How does Jon engage with social media knowing the psychological effects it has? What have been some major breakthroughs for him? Why does Jon believe having kids has made him a better founder? Why does Jon believe that older entrepreneurs are actually more successful than younger founders?

5.) What is Jon's biggest advice to founders when it comes to building relationships with VCs? Should founders "always be raising"? How transparent should founders be with VCs both in the relationship building process and the fundraise itself?

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

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

May 13, 2019

Mamoon Hamid is a Partner @ Kleiner Perkins, one of Silicon Valley's most prestigious venture firms counting Google, Airbnb, Amazon, Spotify, Square and many more $Bn companies among their portfolio. As for Mamoon, he has invested in and served on the boards of some of the most innovative software companies of recent times including Box, Figma, Intercom, Netskope, Slack and Yammer. Prior to joining Kleiner Perkins, Mamoon was a Co-Founder and General Partner at Social Capital and before that Mamoon was a Partner at U.S. Venture Partners (USVP), where he spent six years.

In Today’s Episode You Will Learn:

1.) How did Mamoon make the transition from electrical engineer to VC and how did that translate to his role today as Partner @ KPCB?

2.) With Kleiner's new $600m early stage fund, Mamoon had a blank canvas, how does Mamoon think about portfolio construction from a bottom-up perspective? Why is that strategy optimal? How important does Mamoon believe it is for VCs to have a sector focus today? What does he mean when he says, "VCs need to have both majors and minors"?

3.) In today's heated early stage ecosystem, how does Mamoon analyse and reflect on his own price sensitivity? What deal has changed the way he thought about price and he either regrets not paying it or is thrilled he did pay it? How does Mamoon feel about the compressed fundraising timelines we are seeing today? Is this a concern?

4.) How does KPCB think about reserve allocation with the new $600m fund? How do they approach the opportunity cost of dollar deployment in terms of when to stop following on? How does the investment decision-making process change when comparing initial to reserve investment?

5.) Where does Mamoon believe that founders need the most help from their venture investors? Where does Mamoon see the commonalities in founders struggles to scale themselves with their role? What are the biggest mistakes Mamoon sees being made when initial traction has been hit and they start to scale? How can founders avoid these?

6.) How does Mamoon think about and address what it takes to build the most successful and efficient venture partnership? How does Mamoon compare this to a basketball team? Is venture really a team sport today? what are some of the biggest challenges in scaling venture firms over time?

Items Mentioned In Today’s Show:

Mamoon’s Fave Book: Principles: Life and Work by Ray Dalio

Mamoon’s Most Recent Investment: Viz.ai

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

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

May 10, 2019

Michele Romanow is the Founder & CEO @ Clearbanc, the startup that provides entrepreneurs capital to grow without giving up a piece of their company. In 2019 alone, Clearbanc plans to invest $1B in 2,000 companies. To fund these ambitious plans, they have backing from some of the best in the business including Founders Fund, Santi @ Emergence, Social Capital, Precursor Ventures and Y Combinator just to name a few. As for Michele, prior to Clearbanc, she founded SnapSaves, a leading mobile savings platform that was acquired by Groupon. Before Snapsaves, Michele founded Buytopia, one of Canada’s leading e-commerce companies with over 2.5m customers. If that was not enough Michele is also a Dragon on Dragons Den Canada, the youngest dragon ever.

In Today’s Episode You Will Learn:

1.) How Michele made her way from serial entrepreneur with exits to Groupon and being a Dragon on Dragons Den to changing the way we fund today's businesses with Clearbanc?

2.) Why does Michele fundamentally believe we need to rethink the way we fund our businesses? Why does giving away equity to buy FC and Google ads not make sense? What is the solution? What types of business with what types of revenue does this work for? Why does Michele believe we need to fundamentally stop celebrating fundraisings?

3.) So if Clearbanc lends on repeatable revenue from Google and Facebook, how does Michele think about the volatility of CACs we see as businesses progress? Is Michele concerned by the large incumbents pushing up CACs on traditional platforms? Investors can also be wise strategic advisors, how does Michele think about the potential loss of these advisors and board members with an alternative financing mechanism?

4.) From Clearbanc's data, what have been the big learnings on how venture is currently distributed across the US? To what extent does Michele believe that unconscious bias pervades into the decision-making of much of venture? What have Clearbanc discovered in terms of the diversity of the founders they back, purely through objective data analysis of their businesses?

5.) How does Michele respond when shit hits the fan? What is her coping mechanism? How would Michele advise young founders today in coping with tough times? What were Michele's lessons from her first sturgeon caviar business not being a success?

Items Mentioned In Today’s Show:

Michele’s Fave Book: Little Black Stretchy Pants

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

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

Want to book your own travel and not have the admin team chasing you for every receipt? Take your business travel program to the next level with TravelPerk. They’ve built the world’s largest inventory of low-cost flights, hotels, airbnb, trains, cars, you name it, all in one gorgeous booking experience. AND they’re built for business. Book, manage, support, analyze, and optimize your business travel, all in one place. Add to this a support team made up of dedicated travel experts who deliver a 7-star experience around the clock, and you’re taking corporate travel out of the dark ages. 20VC listeners can score a free lounge pass to over 1200 airports for a whole year. Not only will you be able to add “company savior” to your email signature, but you can also enjoy the luxury of amazing airport lounges all over the world. Click here to find out more!

May 6, 2019

Brendan Wallace is the Co-Founder and Managing Partner @ Fifth Wall, the fund with the core thesis being the physical world around us is colliding with technology. Within their portfolio is the likes of Lime, OpenDoor, Clutter, ClassPass, Lyric and Hippo just to name a few. As for Brendan, before co-founding Fifth Wall he co-founded Identified, a data & analytics company focused on workforce optimization that was acquired by Workday in 2014. Prior to that, Brendan co-founded Cabify, the largest ridesharing service in Latin America. If that was not enough, Brendan has been an active angel investor having led over 60 angel investments including Bonobos, Dollar Shave Club, Lyft, SpaceX, Clutter, Philz Coffee and Zenefits.

In Today’s Episode You Will Learn:

1.) How Brendan made his way from founding the largest ridesharing platform in Latin America to changing the face of early stage real estate and consumer retail investing with Fifth Wall?

2.) What is really going on in retail today? Is "retail apocalypse" a fair term to give to the landscape today? What formats does physical retail no longer work for? What is it perfect for? How does Brendan think about the distribution of physical retail for emerging brands? Will they need 1,000s of stores or is the 1,000 store brand era over?

3.) Why do digitally native brands fundamentally need retail? How much of consumer US spend relies on physical retail still today? When do these DNVB's need to expand into physical retail? From speaking to DNVB CEO's what are the most common challenges they face when making the expansion?

4.) How does expanding into physical retail change the game in terms of customer acquisition for DNVBs? At what point do DNVBs hit the invisible asymptote where acquiring customers through traditional online channels is no longer efficient? How have Amazon impacted the CACs for DNVBs in recent years?

5.) Given the consumer retail focus of the fund, one would expect a lower loss ratio, is it right to assume the lower loss ratio? How does Brendan think about portfolio construction with the fund? How does reserve allocation differ when investing in physical retail vs pure software plays? Is Brendan concerned by the lack of downstream capital in the physical retail space?

6.) How does Brendan assess outcome potential when comparing physical retail to pure software plays? Why des Brendan believe we will see a ton of intermediate outcomes? How does this change the type of entrepreneur that Brendan looks to back with the retail fund?

Items Mentioned In Today’s Show:

Brendan’s Fave Book: The Great Gatsby

Brendan’s Most Recent Investment: Heyday

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

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

Want to book your own travel and not have the admin team chasing you for every receipt? Take your business travel program to the next level with TravelPerk. They’ve built the world’s largest inventory of low-cost flights, hotels, airbnb, trains, cars, you name it, all in one gorgeous booking experience. AND they’re built for business. Book, manage, support, analyze, and optimize your business travel, all in one place. Add to this a support team made up of dedicated travel experts who deliver a 7-star experience around the clock, and you’re taking corporate travel out of the dark ages. 20VC listeners can score a free lounge pass to over 1200 airports for a whole year. Not only will you be able to add “company savior” to your email signature, but you can also enjoy the luxury of amazing airport lounges all over the world. Click here to find out more!

May 3, 2019

Frederic Kerrest is the Founder & COO @ Okta, the independent and neutral platform that securely connects the right people to the right technologies at the right time. To date Frederic has raised over $415m with Okta from some of the best in the business including Doug Leone @ Sequoia, Marc Andreessen @ a16z, a dear friend of the show in Mike Maples @ Floodgate, Aneel Bhusri @ Greylock and Vinod Khosla, just to name a few. Okta IPO'd in April 2017 at a stock price of $17, today they sit at $102. Before founding Okta, Frederic enjoyed roles with Hummer Winblad on the other side of the table as a VC and also at Salesforce and Sun Microsystems on the operations side.

In Today’s Episode You Will Learn:

1.) How Frederic came to found the now public Okta having spent time with Salesforce, Sun Microsystems and Hummer Winblad as a VC?

2.) What about an idea makes it worth pursuing and investing in? Does Frederic agree with the advice he was given, "it is 70% market, 20% people and 10% product"? When evaluating a market, what characteristics make for the most attractive markets? How does Frederic think about insertion points into markets? How does he evaluate market adjacencies? Why is it so good to be a monopolist in a small market?

3.) What were some of the hardest times Okta went through? How does Frederic determine the balance between vision and realism? How does Frederic as the leader personally deal with these challenging times? How can a founder determine from their hiring process whether they have product-market fit? What were the key turnings points that contributed to Okta's success? What did you have to get right to keep scaling?

4.) A little birdy told me there was an amazing story behind the a16z investment, what is that story? How did Frederic meet Marc and Ben and how did his relationship with them evolve over time? When analysing his investor base, where did each add real strategic value? What advice does Frederic give to founders today on the theme of investor selection? What should the core considerations be?

Items Mentioned In Today’s Show:

Frederic’s Fave Book: Battle Cry of Freedom: The Civil War Era

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

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

Apr 29, 2019

Sarah Smith is a Partner @ Bain Capital Ventures, a leading US venture fund with a portfolio that includes the likes of LinkedIn, Lime, SendGrid, Jet.com and more incredible companies. As for Sarah, what a start she has had to her time at Bain leading investments in the likes Perksy and the unicorn that is Lime. Prior to joining Bain, Sarah spent 5 years at Quora both as VP of Advertising Sales and Operations and then also from 2012-2016 as VP of HR, Recruiting, and Operations scaling the company from 40 to 200 employees. Before Quora, Sarah spent 4 years at Facebook as Director of Online Operations where her team scaled revenue to $1 billion ARR while reducing churn and increasing customer satisfaction.

In Today’s Episode You Will Learn:

1.) How Sarah made her way into the world of venture having seen the hyper-growth of both Facebook and Quora over 9 years in operations? What were the biggest takeaways from her time with Facebook and Quora? What lessons did Sarah learn as an elementary school music teacher that she has applied to her role in VC?

2.) Sarah and Bain led the Series D in Lime, so how does Sarah think about:

  • Market Size: How did Sarah think about and assess market size when evaluating Lime? How does Sarah respond to Peter Fenton's statement, "I always laugh when I hear investors say they look for big markets"?
  • Competition: How did Sarah look to get comfortable entering such a fiercely competitive space? Is capital itself a defensible moat?
  • Dilution: With such huge future funding requirements for these companies, how did Sarah get comfortable with the level of dilution that will surely occur?
  • Hardware & Unit economics: How does Sarah think about and respond to the current level of break rates? How does Sarah believe Lime can have positive unit economics within 18 months?

3.) Why does Sarah believe that engineers are fundamentally underpaid? How does this tie into their mindset and attitude to equity? Why does Sarah believe the 4-year vesting schedule is fundamentally outdated? What would Sarah advise founders in terms of comp package to put in it's place? Does Sarah believe the high attrition rate in the valley is a feature or a bug?

4.) Why does Sarah believe it is glib to say the lack of equality is merely the problem of VC being an old boy club? What are the more foundational and systemic problems that have caused this inequality? Why does GP commit fundamentally inhibit diversity? For firms looking to add a female partner, what is their literal next step? What does that process look like? What can they do to ensure their success in the first year? Where does Sarah see many firms going wrong here? What must firms avoid?

Items Mentioned In Today’s Show:

Sarah’s Fave Book: Brotopia: Breaking Up the Boys' Club of Silicon ValleyThe Making of a Manager: What to Do When Everyone Looks to You

Sarah’s Most Recent Investment: Perksy

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

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

Apr 26, 2019

David Rogier is the Founder & CEO @ Masterclass, the startup that brings you online classes taught by the world's greatest minds including Steve Martin, Natalie Portman, Margaret Attwood and more. To date, David has raised over $140m in funding for Masterclass from the likes of IVP, NEA, Javelin, Michael Dearing @ Harrison Metal, Atomico and past guests of the show Sam Lessin and Philip Krim. As for David, prior to founding Masterclass, he was on the other side of the table as an investor with Harrison Metal. Before venture, David spent time with IDEO helping to create new consumer products and brands.

In Today’s Episode You Will Learn:

1.) How David made his way into the world of startups? How a lesson from his grandmother when he was only 7 shaped the type of company David wanted to build?

2.) David has previously said, "as a founder, you have one job". What is that job? How does David think about how raising VC changes outcomes? Why does David think many founders approach fundraising the wrong way? What questions must founders always ask a VC pre-term sheet? How can founders do their work and diligence on the VC?

3.) Why does David try at all costs to not send the deck to the VC ahead of meeting? Why can this be damaging? How can founders say no politely? Does David agree with the conventional wisdom that "founders must always be raising"? What is the optimal way to structure relationship building with investors?

4.) What does David mean when he says, "pick your investors as board members, not investors"? What does David believe makes the truly special board members? What were David's biggest learnings from Michael Dearing @ Harrison Metal when it comes to boards? What does David believe are big red flags in potential future board members?

5.) When validating the idea and the product, how does David think founders should use testing to prove their thesis at every stage of the business? Why, if proved, does this automatically secure your funding for the next round? What do VCs like to see in this testing? How does David think about when is the right time to go and raise big?

Items Mentioned In Today’s Show:

David’s Fave Book: Creativity Inc

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

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

Apr 22, 2019

Jeremy Liew is a Partner @ Lightspeed Venture Partners, one of the leading firms of the last decade with a portfolio including the likes of Snapchat, Mulesoft, Max Levchin’s Affirm, AppDynamics and many more incredible companies. As for Jeremy, he is best known for being the 1st investor in Snapchat and has also led investments in StitchFix, Affirm, Ripple, Giphy and Bonobos just to name a few. Previously, Jeremy was with AOL, first as SVP of corporate development and chief of staff to the CEO, and then as general manager of Netscape. Due to his incredible investing success, Jeremy has been featured on the Forbes Midas List multiple times.

In Today’s Episode You Will Learn:

1.) How Jeremy made his way into the world of venture with Lightspeed and came to be one of the valley's leading consumer investors and minds?

2.) How does Jeremy think about and approach sourcing today? How has mindset on sourcing shifted over the last decade? For a new VC, what would Jeremy advise them in terms of building them benchmark for distinguishing between good and great? How does Jeremy distinguish between good and great? Who does Jeremy believe is the most naturally gifted sourcer and hunter he has worked with?

3.) What does Jeremy mean when he says, "it is more important to be right than contrarian"? From winning some of the hottest deals, what have been Jeremy's lessons on what it takes to win the most competitive? What does he mean when he says, "you have to find your home advantage"? Should investors spend time amplifying their strengths or improving their weaknesses? How does Jeremy think about the round compression timelines on hot deals today? How can investors and founders build relationships fast?

4.) Why does Jeremy believe that founder to VC engagement can be similar to a driving instructor and student? What are the biggest mistakes startups make when they hit initial traction and start to scale? WHat patterns has Jeremy seen? How can founders avoid them?

5.) How does Jeremy fundamentally structure his week and time? What time is devoted to internal meetings and partnership meetings? How much time is allocated to the existing portfolio? How much time is spent with new prospective companies? What is Jeremy's favourite and least favourite activities within the role?

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

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

Apr 19, 2019

Dylan Field is the Founder & CEO @ Figma, the startup that provides a better way to design, prototype and collaborate, all in the browser. To date, Dylan has raised over $82m in funding from some of the world's best investors including Sequoia, Greylock, Kleiner Perkins, Founders Fund, Index Ventures and more. Prior to changing the world of design with Figma, Dylan held roles at Flipboard, Microsoft and LinkedIn and was part of the renowned Thiel Fellowship.

In Today’s Episode You Will Learn:

1.) How Dylan made his way from Thiel fellow to changing the world of design and prototyping with Figma?

2.) What is the story behind the 4-year journey to the launch of their first product? How did Dylan maintain morale with such an extended window between creation and launch? What are the core challenges of building tools companies and getting initial traction? How did Dylan satiate VCs desire for fast growth with such a long period to launch? Is it possible to "go slow to go fast" with VC dollars?

3.) Sequoia led Figma's Series C, how did the round come together? What was it that made Dylan choose the lead investors for each of his rounds? How did this round compare to prior rounds led by Index, Kleiner and Greylock? How does Dylan advise founders to build relationships of trust and transparency with their VC in short period of time?

4.) How did Dylan approach the topic of board construction? What did he most want to get out of his board? What have been some of Dylan's biggest learnings when it comes to board management? What has Dylan found the most challenging element?

5.) As a young founder himself, where does Dylan see commonalities in the mistakes that other young founders make today? As a young founder, how has Dylan been able to hire A** talent execs? What have been some of the biggest learnings on team assembly and construction through the process?

Items Mentioned In Today’s Show:

Dylan’s Fave Book: Stronger, Faster, and More Beautiful

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

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

Apr 15, 2019

Dave Sobota is the Vice President of Corporate Development @ Instacart, the company that delivers your groceries in as little as 1 hour. To date the company has raised over $1.9Bn in funding from some of the very best investors and operators including Mike Moritz @ Sequoia, Jeff Jordan @ a16z, Aaron Levie @ Box, Sam Altman, Garry Tan and more incredible names. As for Dave, prior to Instacart, he was Director of Corporate Development @ Google for over 10 years and before that was with leading law firm, Wilson Sonsini.

In Today’s Episode You Will Learn:

1.) How Dave made his way from the world of law to Director of Corporate Development at Google to his position at Instacart today?

2.) In 2016, we had 513 BC backed exits, 499 were M&A, so how does Dave assess the M&A landscape today? Why id Dave bullish on the future M&A environment, at least for the next 12 months? Where are his concerns around M&A clustering? How does Dave view the entrance of large scale PE into the tech M&A arena?

3.) From leading Google's M&A practice, what have been Dave's core learnings on whether an entrepreneur should sell their company or remain independent? Paul Graham once said, "startups only talk to corp dev when they are doing really well or really badly". Does Dave agree? What are the reasons a startup would not speak to corp dev? What is the right way for them to communicate this while leaving the door open for future conversations?

4.) How does Dave operationalise the tracking of the startup market and determine what startups he wants to meet? How does Dave like to and think about working with the VC community here? What does that relationship building process look like? In those early meetings, what are the core questions that founders must ask? How much of a role does price play for Dave when considering an acquisition?

5.) How can founders ensure when they sell their company, that it will be properly integrated? What answers from the acquirer suggest it will or will not be? From countless M&A processes, what do the best integrations look like post-acquisition? Where are mistakes often made? Does Dave agree with Paul Graham in stating it is a "gruelling" process?

Items Mentioned In Today’s Show:

Dave’s Fave Book: Lonesome Dove

Dave’s Most Recent Acquisition: Tenor

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Apr 12, 2019

Henry Ward is the Founder & CEO @ Carta, the startup that helps private companies, public companies, and investors manage their cap tables, valuations, investments, and equity plans. To date, Henry has raised over $147m in funding from some of the industries leading investors in USV, Spark, K9 Ventures and Meritech and then also leading founders including Flexport's Ryan Petersen, Transferwise's Taavet Hinrikus and Slack's Stewart Butterfield. Prior to founding Carta, Henry was Founder of SecondSight, a portfolio optimization platform for retail investors.

In Today’s Episode You Will Learn:

1.) How Henry made his way into the world of startups and came to found the gamechanger of cap tables and valuations with Carta?

2.) What does Henry mean by the term "executive half-life"? How does Henry determine between an exec that can scale with the company and an exec that cannot? What are the leading indicators? When weaknesses are revealed, how does this manifest itself? Does the exec open up and admit to it or does the leadership team have to be proactive?

3.) Question from Manu @ K9: As a first time CEO, what have been the biggest personal challenges for Henry in the scaling of himself? Why does Henry think it is unfair founders are given exemption from blame in scaling but execs are not? How does Henry make decisions differently now to the early days? What have been the improvements?

4.) How does Henry buck the conventional wisdom with his willingness to go after very small markets? What does the N of 1 vs 1of N rule mean here? Why does Henry believe the N of 1 markets is the most attractive? What are the core advantages to owning your market? How can founders think about insertion points? When is the right time to add additional products? How does Henry respond to the traditional notion of "focus"?

5.) Why does Henry believe most founders are afraid to put investors to work? If fundraising is, as Henry suggests "an auction process", what can founders do to optimise it? How does Henry approach the element of value creation and value extraction? How does this influence his approach to pricing? How does Henry think more tech founders can leverage acquiring services businesses and automating their processes over time? Where is the arbitrage in pricing here?

Items Mentioned In Today’s Show:

Henry’s Fave Book: The Essays of Warren Buffett: Lessons for Corporate America

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

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

Apr 8, 2019

Dayna Grayson is a Partner @ NEA, one of the leading venture firms over the last 4 decades with a portfolio including the likes of Opendoor, Jet.com, Uber, WorkDay, Plaid, Box and many more incredible companies. As for Dayna, she has led the firm's investments in the likes of Desktop Metal, Formlabs, Onshape, Glamsquad, Framebridge and Curalate, just to name a few. Prior to joining NEA, Dayna was an investor at North Bridge Venture Partners where she championed companies including Camiant (acquired by Tekelec) and Tapjoy. Before venture Dayna was an engineer at Eye Response Technologies, later acquired by Dynavox Mayer-Johnson and also a product designer at Blackbaud (BLKB), the leading global provider of software to nonprofit organizations.

In Today’s Episode You Will Learn:

1.) How Dayna made her way into the world of venture and came to be a Partner at NEA from her roots in product design and engineering?

2.) Sourcing: How does Dayna approach the sourcing component of venture today? What does the deck filtering process look like to Dayna, prior to meeting? What has Dayna found works best in really building rapport in the first meetings? What does the conviction building process look like for Dayna from there? If negative, how has Dayna found is the most effective way to say no?

3.) Decision-Making: How does Dayna think about optimising the investment decision-making process? How does Dayna balance between data vs gut? Does NEA require unanimous decision-making? Why does Dayna believe that at A or earlier, the price really does not matter? When does price really become a big issue?

4.) Evolution of Expectations: How does Dayna believe entrepreneurial expectations of VC has changed over the last decade. Where does Dayna believe investors can really provide the most value? Which board member has been the most impressive to Dayna when sitting alongside them on the board? Why?

Items Mentioned In Today’s Show:

Dayna’s Fave Book: Dopesick: Dealers, Doctors and the Drug Company that Addicted America

Dayna's Most Recent Investment: WhireWheel

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

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

Apr 5, 2019

Jeff Russakow is the CEO @ Boosted, the startup producing vehicle grade electric skateboards rethinking how we travel. To date, they have raised $74m in funding from the likes of Khosla Ventures, iNovia Capital, Andreessen Horowitz and our friends at Initialized. Prior to Boosted, Jeff was CEO @ Gimbal where he doubled revenue in his first year and added 80 new enterprise clients. Before that, Jeff was the CEO @ Findly where he grew the company to 450 employees and 20m end users. Jeff also enjoyed prior roles with the likes of Symantec, Adobe, SAP and Yahoo.

In Today’s Episode You Will Learn:

1.) How Jeff made his way from leading enterprise CEO to re-thinking the way we travel today as CEO of Boosted?

2.) How does Jeff analyse the current sentiment to fundraising in the valley, specifically with regards to business construction? How has Jeff seen the investor class fundamentally transition over the last 20 years? When approaching investor selection, what is the 1 question that Jeff always asks? Where do founders often make mistakes here?

3.) Having raised the $60m round in 2018, how does Jeff approach the theme of capital efficiency today with Boosted? How does Jeff determine when is the right time to pour fuel on the fire? Why is Series B often the most challenging phase when considering the focus on unit economics and vision simultaneously?

4.) What is Jeff's gut reaction to the statement, "hardware is hard"? Why does Jeff feel this to be a glib statement that misses the point? How does Jeff respond to the criticism of the commodity element of hard, easy to replicate and copy? How would Jeff like to see the investor class change their mindset to hardware? What is the right way to approach it?

5.) What are the core elements required for a successful CEO transition? For a potentially incoming CEO, what must they be wary of with regards to the information conveyed to them by investors of the company? Where has Jeff seen many go wrong in CEO transitions? What can the founders do to make this process as smooth as possible?

Items Mentioned In Today’s Show:

Jeff’s Fave Book: The Missing Piece 

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Apr 1, 2019

Garry Tan is the Co-Founder and Managing Partner @ Initialized Capital, one of the West Coast's leading early-stage funds with a portfolio including the likes of Coinbase, Instacart, Cruise, Flexport and Opendoor, just to name a few. As for Garry, before co-founding Initialized, he was a partner at Y Combinator for nearly five years where he advised and funded over 600 companies. He was also co-founder of YC-backed blog platform Posterous (acquired by Twitter in 2012). Before that he was employee #10 at Palantir, where he was a founding member of the engineering team for Palantir's financial analysis product, and also fun fact, Garry designed Palantir's logo.

In Today’s Episode You Will Learn:

1.) How Garry made his way from Founder and YC Partner to managing over $500m AUM today with his leading of Initialized? How did Garry's investment mindset change with the transition from angel to an institutional investor?

2.) What does Garry believe is the one thing pre-seed and seed investors must do that is more important than anything else? What relationship to the very best founders have with failure? How do they think about and approach it? How has Garry seen his own conviction building process in founders change over time? How does Garry approach the turning down of opportunities? What is the right way to deliver that feedback?

3.) Ownership: Initialized's funds have scaled from Fund I being $7m to Fund 4 being $225m, how have their ownership requirements changed with the evolution of their fund size? How does Garry think about collaboration and co-opetition with others funds as a result? What are the core challenges here?

4.) Price Sensitivity: With the larger fund and slightly more flexibility, how does Garry evaluate his own price sensitivity? What deal has Garry passed on due to price and it has stuck with him and taught him a valuable lesson? On pricing, how does Garry and Initialized approach reserve allocation?

5.) Investment Decision-Making: Garry has previously said "decision-making is a differentiator", what do Initialized do to ensure the highest quality of internal discussion and decision-making? How do they approach unanimous vs single partner decision-making? How does Initialized approach internal attribution with this in mind?

Items Mentioned In Today’s Show:

Garry’s Fave Book: Peter Thiel's Zero To OnePaul Graham's Hackers and Painters

Garry’s Most Recent Investment: Standard Cognition

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

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

Mar 29, 2019

Joel Gascoigne is the Co-Founder & CEO @ Buffer, the social media management tool that makes it easy for businesses and marketing teams to schedule posts, analyze performance, and manage all their accounts in one place. They had raised both seed and Series A rounds but last summer, spent $3.3m to buy out the majority of their Series A investors, making them much more independent. Joel now runs Buffer as a profitable business with $2m in profit in 2017 and $3m in 2018. Before co-founding Buffer, Joel co-founded OnePage and StartupMill and was a web developer in the UK.

In Today’s Episode You Will Learn:

1.) How Joel made his way from web developer in the UK to founder of Buffer, in 2018 a business that did $3m in profit?

2.) What does Joel mean when he says that "fundraising is a bigger decision than most people realise"? At what moments does Joel believe that the founders are no longer the boss? When did Joel feel he was no longer the boss? What does Joel wish founders knew more about the VC process and mechanics? What questions must they ask VCs?

3.) Would Joel agree with Anand Sanwal, previously on the show that "VCs foie-gras their startups", forcing synthetic growth? What is the right way for founders to respond to this pressure? How did Joel personally handle the pressure? How does Joel assess and analyse the current VC ecosystem? What would he most like to change?

4.) There was a time when individuals did not want Joel to be CEO, how did Joel deal with that? What would Joel advise founders in the same position? What are the right steps to take? Joel then lost his co-founder, how was that process for Joel? What does he know now that he wishes he had known at the beginning of that process? How does he look to retain that level of support and guidance from someone other than a co-founder?

5.) What does Joel mean when he says, "leaders must lean into transparency"? Are there any limitations to being overly transparent? Now as a profitable company, how does Joel think about profit sharing with the team? What does profitable status allow the team to achieve and do that is not normally possible for VC backed co's?

Items Mentioned In Today’s Show:

Joel’s Fave Book: A Little Life

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

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

Mar 25, 2019

Alex Clayton is a Partner @ Spark Capital, one of the leading firms of the last decade with a portfolio including the likes of Slack, Postmates, Oculus, Cruise, Twitter, the list goes on. As for Alex, he co-led Spark's investments in Pendo and Outreach and then led Spark's investments in Justworks, Braze (Appboy) and JFrog. Before Spark, Alex spent three years at Redpoint Ventures as a senior associate where he sourced or was actively involved in the firm's investments in Duo Security, JustWorks, RelateIQ (Salesforce.com), Infer, Lifesize and Sourcegraph. Prior to joining Redpoint, Alex was in the TMT investment-banking division of Goldman Sachs where he worked with Intuit, Yelp, SanDisk, and others. Fun fact, in the past Alex played on the ATP World Tennis Tour, competing in the U.S. Open and many other ATP events.

In Today’s Episode You Will Learn:

1.) How Alex made his way from the world of investment banking with Goldman Sachs to one of the valley rising stars in the world of enterprise investing? What were Alex's biggest takeaways from his time at Redpoint and working with Tom Tunguz?

2.) How does Alex think about and approach sourcing today? How does Alex find most of his deals? How does Alex breakdown both thesis and network driven sourcing? How does sourcing at growth differ to sourcing at the early stage? If Alex has to meet founders when they are not raising, what does Alex advise founders who are told that you should not "always be raising"?

3.) How does Alex think about market sizing and evaluation today? What does he mean when he says he closely examines "market depth"? How does Alex determine whether a company has the ability to scale from a niche into a much larger TAM? What are the risks Alex is willing vs not willing to take when it comes to market?

4.) How does Alex think about competitor analysis when evaluating an opportunity today? In a world of almost infinite capital, does Alex believe that cash alone is a significant moat for competition? In customer calls when they discuss competition, what excites Alex to hear? How does Alex structure those customer reference calls?

5.) Alex has studied some of the best in class when it comes to SaaS, what do the best in class look like when it comes to: 1.) Quota attainment. 2.) Payback period. 3.) Net dollar retention and churn? 4.) Capital efficiency? Growth rate? Ultimately, what does Alex believe that it takes to go public having studied so many S1s?

Items Mentioned In Today’s Show:

Alex’s Fave Book: Zero to One by Peter Thiel

Alex’s Most Recent Investment: Braze

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

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

Mar 18, 2019

Mike Hirshland is the Co-founder of Resolute Ventures, one of the leading pre-seed and seed stage funds of the last decade having recently announced their new $75m Fund IV. In prior funds they have the likes of OpenDoor, Mixmax, Greenhouse, AppZen and more incredible companies. As for Mike, prior to founding Resolute, he founded Dogpatch Labs, the community which helped launch over 350 companies including Instagram. Before Dogpatch, Mike was a partner with Polaris Venture Partners from 1999-2011, where he was the original seed investor behind Automattic, Q1 Labs (acquired by IBM for $600 million), Quantcast and KISSmetrics.

In Today’s Episode You Will Learn:

1.) How Mike made his way from a legal clerk in the US Supreme Court to founding his own venture firm in the form of Resolute Ventures?

2.) What does Mike mean when he says Resolute invest at the "old seed stage?" What stage of development and traction are the companies at this stage? Why does seed investing out of a $Bn fund not make sense to Mike? What are the acceptable vs unacceptable risks at this stage?

3.) How does Mike think and assess portfolio construction today? How many lines in the portfolio is enough to be sufficiently diversified? How does Mike think about ownership given his thesis on diversification? How does Mike assess his own price sensitivity today? How does Mike think about loss ratio within the portfolio today?

4.) What are the ideal attributes of the founder/VC relationship to Mike? Is it right for the investor to also be friends with their founders? What can founders do to really build and deepen relationships with investors both during and outside of official fundraises? Where does Mike often see founders making mistakes here?

5.) How does Mike think about the right time to establish a board? What does Mike advise founders in terms of board composition in the early days? How does Mike look to build a sense of "board intimacy" with his founders? Why does Mike believe that there is a "counter-productivity to boards at seed"?

Items Mentioned In Today’s Show:

Mike’s Fave Book: A Little Life

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

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

Mar 15, 2019

Adam Pritzker is the Chairman & CEO @ Assembled Brands, a holding company providing working capital and financial services to emerging brands. In October 2018, they raised $100m in development capital from the prestigious Oaktree Capital Management. As for Adam, he is also a co-founder of General Assembly where during his tenure, prior to its acquisition by Addecco Group, he served as Chief Creative Officer, Chief Product Officer, and Chairman. For his entrepreneurial endeavors, Adam was featured in Forbes’ 30 Under 30, Vanity Fair’s The Next Establishment, Inc. Magazine’s 30 Under 30, and Business Insider’s Silicon Alley 100.

In Today’s Episode You Will Learn:

1.) How Adam made his way into the world of startups with the co-founding of General Assembly and how that led to his founding Assembled Brands and financing the future of brands?

2.) Why is Adam optimistic about the current state of the consumer brand and retail environment? How does Adam respond to Alex Taussig @ Lightspeed's suggestion of the "re-platforming of retail"? How does Adam approach the changing demographic of consumer spend? What does this mean for both the brands and the channels they use to acquire customers? Does Adam believe we are in a consumer bubble today?

3.) How does Adam think about the lack of free and open distribution today for consumer companies? Are the traditional channels now too expensive to acquire customers on? How does Adam advise consumer founders on the saturation rate of marketing channels? How can they foresee the ceiling ahead of time?

4.) Adam has previously stated that Instagram is the new QVC, what did he mean by that? What type of consumer brand is Instagram best suited for? Why does Adam believe that in many cases the venture financing method is suboptimal and wrong for these scaling brands? What can founders who have taken VC funds and now seen it was potentially a mistake do?

5.) Why does Adam believe that the "infrastructure to power emerging brands is broken"? How can the current stack and infrastructure for brands be improved? What metrics should consumer founders really hone in on today? What sort of metrics suggests a brand is VC backable vs is not VC backable? How does Adam think about the ability of the consumer brand space to provide venture returns at scale?

Items Mentioned In Today’s Show:

Adam’s Fave Book: (1.) The Coddling of the American Mind: How Good Intentions and Bad Ideas Are Setting Up a Generation for Failure(2.) The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It

Adam's Most Recent Investment: Felix Gray 

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

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

Mar 11, 2019

Victoria Treyger is a General Partner & Managing Director @ Felicis Ventures, one of the leading venture firms of the last decade backing 2 unicorns per year since founding including Shopify, OpenDoor, Flexport, Adyen, Twitch, Fitbit and many more. At Felicis, Victoria led the firm’s investments in prior 20VC guest Assaf Wand @ Hippo, Sentio, Sentilink, Blume, Floravere, and other stealth brands. Prior to joining Felicis, Victoria was Chief Revenue Officer of Kabbage. During her six-year tenure, Victoria and her team were instrumental in scaling revenue into the hundreds of millions of dollars and delivered a compound annual growth rate of over 100%. Victoria’s deep operating experience also includes leadership roles at Amazon, American Express, Travelocity, and RingCentral.

In Today’s Episode You Will Learn:

1.) How Victoria made her way into the world of VC as GP @ Felicis today having scaled revenue into the 100s of millions with Kabbage on the operating side of the table?

2.) Having just made the move from the world of operations, what are the most surprising aspects of venture? What elements have you found to be the most challenging? How does Victoria think about what it takes to be the most effective coach? What can the investor do to build that level of trust and transparency with the founder?

3.) In terms of being a board member, how involved does Victoria think the board member should be? Who is the best board member Victoria has worked with? What made them so special? What are Victoria's biggest pieces of advice to founders when it comes to how to run an efficiency board? What is the right way for founders to think about board composition?

4.) What 3 trends in the world of consumer and CPG make Victoria so excited to be investing in the space today? What has fundamentally changed about the distribution of those products that changes the way we consume the products? Does this mean Victoria would disagree we are in a D2C bubble today?

5.) Speaking of distribution, how does Victoria respond to the suggestion "there is a lack of free and open distribution today" with customer acquisition costs being so expensive? How does Victoria think about the consumer and CPG space's ability to provide venture returns at scale moving forward?

Items Mentioned In Today’s Show:

Victoria’s Fave Book: Mindset: How You Can Fulfil Your PotentialPersonal History

Victoria’s Most Recent Investment: SentiLink

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

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

Mar 8, 2019

Austen Allred is the Founder & CEO @ Lambda School, a 9 month, immersive program that gives you the tools and training you need to launch your new career—from the comfort of your own home. As a Lambda student, you pay nothing until you’re earning $50k or more. And if you don’t, it’s free. To date, Austen has raised over $48m with Lambda from a personal favourite of mine Bedrock, GGV, GV, Stripe and Ashton Kutcher just to name a few. Prior to founding Lambda, Austen was Senior Manager for Growth @ LendUp and before that co-founded Grasswire.

In Today’s Episode You Will Learn:

1.) How Austen made his way from being broke, sleeping in a car to founding one of Silicon Valley's hottest startups in the form of Lambda School?

2.) Austen lived in his car for many months in Palo Alto, what did Austen come to learn about himself from that experience? Before Austen has said, "it is not about money", so how would Austen describe his personal relationship to money? Consequently, what does this mean for Austen's relationship to risk?

3.) Austen previously stated he was "determined to never raise VC again before Lambda School". 2 years and $47m later, what changed in his attitude to raising VC? How mus every founder examine their business model before raising VC? What is the one question they must ask pre-raise?

4.) Austen recently raised a $30m Series B round, how did that round come about? What is Austen's biggest advice when it comes to investor selection? How does Austen think about when is the right time to raise big? How does that impact and affect operating mentality? What was it about Geoff Lewis that made Austen take his offer over others?

5.) Question from Geoff @ Bedrock: How does Austen iterate on all aspects of the business so fast? Why does Austen believe that the speed and quality of decisions are not mutually exclusive? Why does Austen believe the faster you ship, the higher quality they will be? How does Austen determine which experiments to stick with vs drop?

Items Mentioned In Today’s Show:

Austen’s Fave Book: Les MiserablesThe Wright Brothers

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

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

Mar 4, 2019

Jeff Richards is Managing Partner @ GGV Capital, one of the leading venture firms of the last decade with a portfolio including the likes of Alibaba, Slack, Square, Xiaomi, Peloton, OpenDoor, just to name a few. As for Jeff, he sits on the board of or is an observer at BigCommerce, Brightwheel, Gladly, Lambda School, Namely and Tile just to name a few. Jeff also led GGV’s investments in Buddy Media (acquired by Salesforce), HotelTonight, Flipboard and has been actively involved in GGV’s investments in Opendoor, Domo, Square and Wish. Prior to joining GGV, Jeff founded two software companies: R4 (acquired by VeriSign), and QuantumShift, backed by Texas Pacific Group (TPG).

In Today’s Episode You Will Learn:

1.) How Jeff made his way into the world of VC with GGV from founding and scaling 2 software companies in the 90s? What were Jeff's 2 biggest takeaways from having the company he founded raise over $100m then go to $0 in the crash?

2.) How does Jeff approach and see the transition from founder to CEO today? When does this transition need to occur? How do first-time founders differ compared to experienced serial entrepreneurs when it comes to building their teams? Where do they often struggle or make mistakes? What advice does Jeff offer them?

3.) Jeff has previously said, "do not raise for the highest valuation", what is his thinking here? What specific examples does Jeff have of why it can hurt and damage both the founder and the company? How does Jeff think about his own price sensitivity today? How does he determine when a stretch is a stretch too far? From backing the likes of Alibaba, Xiaomi and Didi, what were his biggest takeaways when it came to price?

4.) Decision-making is one of the only products venture has, how does Jeff and GGV approach decision-making as a firm today? Being a slightly later stage firm, how do they think about reserve allocation? What does the re-investment decision-making process look like? How does GGV think about attribution as a firm today? What are the benefits?

5.) What advice would Jeff give to an individual that has just entered VC? What does Jeff know now that he wishes he had known at the beginning? How does Jeff think about what it takes to be a truly special board member? What one or two things can a board member do to move the needle in their relationship with their founder?

Items Mentioned In Today’s Show:

Jeff’s Fave Book: In an Uncertain World: Tough Choices from Wall Street to Washington

Jeff’s Most Recent Investment: Lambda SchoolElectric

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

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

Mar 1, 2019

Rob Sadow is the Founder & CEO @ Scoop, the startup that dramatically improves your commute providing convenient carpools with co-workers and neighbours. To date, Rob has raised over $37m in funding for Scoop from the likes of Danny Rimer @ Index, Brook Porter @ G2VP, Zaw Thet @ Signia Venture Partners and BMW i Ventures just to name a few. Before founding Scoop, Rob was a Manager @ Bain & Company and before that spent time in Israel with Better Place, working to provide electric vehicle networks to help accelerate the global transition to sustainable transportation.

In Today’s Episode You Will Learn:

1.) How Rob made his way from the world of consulting and Bain to founding the future of convenient commutes with Scoop?

2.) How does Rob approach key decisions? What does Brook Porter @ G2VP mean when he says, "from a first principles perspective"? How does Rob determine when to make decisions with the head or the heart? Does Rob agree with Fred Destin, "as a founder, decisions are never perfect, it is about batting average"? Where does Rob see many make mistakes when it comes to decision-making?

3.) How does Rob find the dynamics of working with his brother as his co-founder? What are some of the core challenges? How does one make it scale and how does the relationship need to change over time? What is Rob's biggest advice to others when thinking about the person they partner with?

4.) How does Rob think about board construction? What have been some of Rob's biggest lessons in really using your board to get the most out of them? What works well for this? What does not work? How can founders create this level of relationship with their board members? Should founders direct their ask to specific individuals when soliciting help from their board?

5.) Why does Rob believe that they have next to no attrition of employees at Scoop? What have been some of Rob's biggest lessons when it comes to both culture creation and maintenance? How does Rob think leaders can invest more in their employees? What does this look like? Where do many go wrong or misallocate?

Items Mentioned In Today’s Show:

Rob’s Fave Book: The Wheel of Time

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

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

Feb 25, 2019

Frank Chen is a Partner @ Andreessen Horowitz, one of the world's most prestigious venture firms with a portfolio including the likes of Airbnb, Coinbase, Github, Lyft, Slack and many more incredible companies. As for Frank, prior to joining the world of venture, he was a VP of Products & UI Design at HP Software and before that held the same title at Opsware. Before that, even cooler, Frank was Director of Product Management @ Netscape where he led a cross-functional team that defined, shipped, and marketed Netscape's award-winning LDAP directory and security products. 

In Today’s Episode You Will Learn:

1.) How Frank made the move from the world of operations with Opsware and HP to being a Partner at Andreessen Horowitz?

2.) How does Frank view the current state of play for AI and machine learning? How does the rise of automation shift the economy as we know it? What does it do to class distinctions? How does Frank view it's impact on the labour market? How does Frank think about the value of truly large datasets? Where is the asymptotic moment where the utility value of data is realised?

3.) With the rise of self-driving, how does Frank perceive the future of car ownership? Who will fundamentally own and operate the vehicles? Will it be a horizontal play or a vertical play? In terms of adoption, why is Frank negative towards a driver assisted transition phase and believe in a more binary transition?

4.) How does Frank perceive the rise of automation and self-driving cars impacting public infrastructure? How will the layout of our cities change over time? How does Frank believe urban real estate could be optimised in a more efficient manner? Which nations does Frank believe will be the first to innovate here?

5.) What is the most challenging element of Frank's position as Partner @ a16z? How does Frank think about the right way to say not to an entrepreneur? How does Frank look to scale the learning curve rapidly when investigating new industries? What are the challenges here? What advice would Frank give to someone looking to scale learning curves?

Items Mentioned In Today’s Show:

Frank’s Fave Book: The Chronicles of NarniaThe Lord of The Rings

Frank’s Most Recent Investment: Branch

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

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

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