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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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Jul 19, 2019

Sid Sijbrandij is the Founder & CEO @ Gitlab, a single application for the entire software development lifecycle. From project planning and source code management to CI/CD, monitoring, and security. To date, Sid has raised over $145m in funding for Gitlab from the likes of GV, August Capital, YC, Khosla and Goldman Sachs just to name a few. What is incredible, Sid has scaled the team to over 762 team members across 55 countries and is famed for his openness and transparency on how he builds both the product and company. You can find the fantastic Gitlab handbook here.

In Today’s Episode You Will Learn:

1.) How Sid made his way into the world of startups, learned Ruby in the early days and came to found Gitlab? What was that a-ha moment?

2.) In 2019 Gitlab is growing from 400 to 1,000 people, what are the biggest challenges that come with such operational growth? How does one hire at such pace and retain quality? How does Sid think about the right way to onboard new employees? How does Sid think about KPI and goal setting in the early days? 

3.) Today all 750 Gitlab employees are remote, what does Sid believe is the secret to making remote teams work at scale? How does Sid think about the balance between fast shipping cadence and perfect product releases? Why does Sid believe, "you have to have a low level of shame on the product you release"?

4.) How does Sid think about operating Gitlab as a totally transparent company? What does that mean both in reality and in process? Why does Sid believe it is optimal to have a roadmap that is open for everyone to see? What are the pros? What are the cons of such transparency? How do competitors respond? 

5.) If every great business is bundling or unbundling, where does Sid believe he and Sid are in the process today? How does Sid think about being too much to too many people? How does the open-source community really come into play in the development of Gitlab?

Items Mentioned In Today’s Show:

Sid’s Fave Book: High Output Management

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

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

Jul 15, 2019

Santi Subotovsky is a General Partner @ Emergence Capital, one of the valley's leading venture firms of the last decade focusing on enterprise & SaaS applications. Within their incredible portfolio is the likes of Salesforce, Zoom, Box, Veeva Systems, SuccessFactors and many more. As for Santi, he has led deals in the likes of Zoom, Crunchbase, Clearbanc, Top Hat and Chorus.ai to name a few. Before Emergence, Santi founded AXG Tecnonexo, a SaaS e-learning company in Argentina which he expanded to 150+ employees across Latin America and the U.S. Santi is also a founding board member of Puente Labs, an organization that helps founders of Latin American high-potential growth companies scale their businesses globally.

In Today’s Episode You Will Learn:

1.) How Santi made his way from founding a Latin American EdTech business to being one of the valley's most successful investors of 2019 with Zoom's IPO? What was the biggest barrier he faced when getting into VC? How did he overcome it?

2.) What does Santi believe his superpower as an investor is? What did Santi see in Eric Yuan and the 30 person team at the time that made him believe they would be successful? What made how Eric thinks about presents product so special? What did the relationship building process look like between Eric and Santi in the early days?

3.) How does Santi like to work with his portfolio companies? How does Santi think about time allocation across the portfolio? Why does Santi believe it is crucial to not just spend time with the CEO but the exec team also? Where does Santi most like to provide value and leverage to the CEO? Why does Santi believe all VCs are just sales reps?

4.) Why does Santi believe that a vertically focused fund is the optimal strategy to pursue today? What are the benefits? What are the drawbacks? How does Santi think about the obvious overlap between consumer and enterprise today? With the thematic focus, how does Santi think about loss ratio and batting average? How does Emergence approach the element of both ownership and price? Where do they optimise?

5.) With larger and larger funds, how does Santi see the future of venture? Why does he believe that we will see vertically focused capital-as-a-service? What does this look like in reality? Is Santi concerned by the extended window of privatisation that is now present in today's capital markets? How concerned is Santi by the compression of fundraising timelines and what does that to investor <> founder relationships?

Items Mentioned In Today’s Show:

Santi’s Fave Book: Candide by Voltaire

Santi’s Most Recent Investment: Openpath

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

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

Jul 12, 2019

Joseph Gordon-Levitt is the Founder @ HitRecord, the startup that allows you to be creative, together, encouraging less self-promotion and more collaboration, so you can create things you couldn't have made on your own. To date, Joe has raised funding from some personal favourites of mine in the form of Alex @ Javelin, Masterclass Founder David Rogier, Twitch Founder Kevin Lin and CrossLink Capital just to name a few. Alongside his role with HitRecord, Joe is also an A-List Hollywood Actor and filmmaker starring in some of my favourite films of all time including The Dark Knight Rises, Inception, 10 Things I Hate About You and many many more.

In Today’s Episode You Will Learn:

1.) How Joseph made his way into the world of technology and startups with the founding of HitRecord? How did much of Joe's early acting career inform much of the HitRecord product today?

2.) Having had such success in the acting world, what caused Joe to really push forward with HitRecord? Question from David @ Masterclass: who has been Joe's biggest mentors in his transition to tech? What have been his biggest takeaways from them? How does Joe balance both being an actor and entrepreneur at the same time? What are the challenges?

3.) Why did Joe decide now was the time to raise VC funds for HitRecord this late into the company life? How does Joe approach the element of investor selection? What specific value add did Joe want to see in his potential investor? How did the pitch process go? How does it compare to presenting for a role in the acting world? What was Joe's biggest lesson about what successful technology pitches do?

4.) When Joe thinks about the HitRecord community, what has surprised him the most with the growth of the community? Why have they purposefully decide to never spend on user acquisition or traffic? What is the strategy behind this? What is Joe's biggest advice to individuals wanting to scale their community and the essentials?

5.) How does Joe assess both the content and social media landscape today? Why is the creative spirit of the world being killed by the current ad model of social platforms? How does Joe think this can be countered and where does HitRecord fit into this evolving landscape?

Items Mentioned In Today’s Show:

Joe’s Fave Book: Letters To A Young Poet

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

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

Jul 8, 2019

Byron Deeter is a Partner @ Bessemer Venture Partners where he has established himself as one of the leading investors in SaaS and Cloud authoring the iconic laws on the state of cloud computing. In terms of track record, fourteen of Byron’s investments are valued above one $1 billion, including eight IPOs and counting. Byron's investments include the likes of Twilio, Intercom, SendGrid, Gainsight, Box, DocuSign and many more. Prior to the world of venture, Byron was a Bessemer Founder raising his Series A from them back in 2000 with Trigo Technologies. The company rapidly scaled to profitability and was acquired by IBM.

In Today’s Episode You Will Learn:

1.) How Byron made his way into the world of venture from founding Trigo Technologies and selling to IBM in 2005? How have seeing multiple booms and busts impacted Byron's investment mentality today?

2.) What the heck is going on in cloud today? Is Byron concerned by the very rich multiples being paid in the ecosystem today? How does Byron think about how public market performance impacts his day to day role investing? Why does Byron believe that the floodgate for cloud IPOs is about to burst open?

3.) Having seen so many cloud IPOs, what should founders take from the lessons of those that have already been so successful? With 14 $Bn companies, what does Byron attribute his investing success to today? How does Byron think about what he wants to invest in today? Are we in an entirely new wave of cloud?

4.) As a former founder, how does Byron think that he engages differently with founders than more financial backgrounded VCs? What can board members really do to build that trusted relationship with the founder in the early days? Is it good for founders and board members to be friends? Is there a line of professionalism that has to be drawn?

5.) How has Byron seen his style of board membership change over the last decade? What would his advice be to someone who has just gained their first institutional board seat? What does Byron believe makes the best board members? What founder he has worked with most excels when it comes to board management? What made them so extraordinary?

Items Mentioned In Today’s Show:

Byron’s Fave Book: AI SuperpowersLegacy

Byron’s Most Recent Investment: ScaleFactor

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

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

Jul 5, 2019

Alex Rodrigues is the Founder & CEO @ Embark, the world's leading developer of self-driving trucks. Embark operates the longest automated freight route in the world. To date, Alex has raised over $47m in funding for Embark from some of my favourites in the form of Pat Grady @ Sequoia, Matt Ocko @ Data Collective, SV Angel and Y Combinator, just to name a few. As for Alex, it started early with his winning a World Robotics Championship while he was in Middle School (the championship was for adults). Post that incredible achievement he dropped out of Waterloo, became a Thiel Fellow, worked as a software engineer @ Nuance Communications, before joining Khan Academy as a software engineer and also teaching robotics @ Khan Lab School.

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In Today’s Episode You Will Learn:

1.) How Alex made his way from winning World Robotics Championships while he was in Middle School to founding the leader developer of autonomous trucks in Embark?

2.) Why does Alex believe in the medium to long term, self-driving is still under-hyped? What is the market analysis to support this? How did his meetings with the world's best public markets investors impact his thinking here? How does Alex think about adoption timelines for self-driving? How do investors think about this when investing?

3.) Does Alex believe that when it comes to self-driving vehicles, they will largely be a public utility? What ownership mechanism does Alex expect to see? What are the pros and cons associated with each? How does Alex think about ownership of the data generated through self-driving? How do we balance privacy and public safety?

4.) With such large milestones and proof points in self-driving, how does Alex think about effective goal setting? What are the core KPIs to be driving for? How can they be broken into more meaningful and achievable wins for the team to get around? What is the core challenge to morale maintenance when the challenge is so long term?

5.) Where does Alex see the commonalities in the biggest mistakes that young founders make? What does Alex know now that he wishes he had known at the start? What have been Alex's biggest lessons on hiring the world's best in their respective fields? What have been Alex's biggest takeaways when it comes to successful board management?

Items Mentioned In Today’s Show:

Alex’s Fave Book: High Output Management

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

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

Jul 1, 2019

Pat Grady is a Partner @ Sequoia, one of the world's leading and most renowned venture firms with a portfolio including WhatsApp, Zoom, Stripe, Airbnb, Github and many more incredible companies. As for Pat, at Sequoia he co-leads the firms growth investment team and has been involved with some of the true greats, Hubspot, Zoom, Okta, Qualtrics, the list goes on. Prior to Sequoia Pat spent three years with Summit Partners.

In Today’s Episode You Will Learn:

1.) How Pat made his way from Summit Partners to co-leading Sequoia's growth investment team? Was it intimidating for Pat entering a partnership with Jim Goetz, Don Valentine, Roelof Botha? How did he manage those nerves?

2.) So many different funds and activities, so what is Sequoia focused on today? Where does Sequoia think about their ideal insertion point today? How do they see the deployment of their blended capital across rounds? Does Pat believe in ownership on first check or building ownership over time? How does Pat think about the extended window of privatisation with IPOs being continuously delayed?

3.) Does Pat believe that VC really is a team sport today? Does Pat agree with Josh Kopelman's statement, "I would rather be a better picker of partners than investments"? What are the core requirements, skills and traits that Sequoia looks for when adding to their partnership?

4.) What is the investment decision-making process at Sequoia? How do they feel about unanimity vs conviction based investment decisions? What are the pros and cons of each? What does Pat believe is the most non-obvious investment decision that Sequoia have made? Sequoia run an incredibly rigorous process when investing, how does Pat balance between that level of rigour with the speed to win the deal?

5.) What advice would Pat give to someone that has just gained their first institutional board? What does Pat know now that he wishes he had known when he started in VC? How does Pat think about time allocation across the portfolio? Concentrate on winners or the strugglers are where your reputation is built? Leading Sequoia Growth and with a beautiful family, how does Pat approach work/life balance?

Items Mentioned In Today’s Show:

Pat’s Fave Book: God Friended Me

Pat’s Most Recent Investment: Embark: Revolutionizing Commercial Transport 

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

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

Jun 28, 2019

Steven Galanis is the Founder & CEO @ Cameo, the startup that allows you to book personalised shoutouts from your favourite people. To date, Steven has raised over $65m in VC funding for Cameo from some of the very best in the business including Bedrock, Nicole Quinn @ Lightspeed, Kleiner Perkins and Spark Capital, just to name a few. Prior to founding cameo, Steven was a Senior AE @ LinkedIn and before that was an options trader in Chicago. With their immense success, they have been featured in all major publications including The Ellen DeGeneres Show. Cameo has also been voted as "The Best Place To Work In Chicago" by GlassDoor.

In Today’s Episode You Will Learn:

1.) How Steven made his way from AE @ LinkedIn to revolutionising what an autograph means today with his founding of Cameo?

2.) What does Steven believe is the No 1 reason that startup founders fail with their startup today? Why does Steven believe that you have to give up your job to pursue your startup, even in the earliest of days? What advice does Steven give to founders and young graduates who approach him for advice in the earliest of days?

3.) As the company scales, how does Steven think about and approach role allocation internally? How does he prioritise hiring for them? How does he think about internal upscaling? How has he dealt with letting go of responsibilities and delegating to the team? What are the core challenges here? What does he advise founders facing this?

4.) Steven has said before, "don't let good get in the way of great", what did he mean by this? How does he determine between good enough and a stretch too far? How does Steven think about the statement of hiring for 6 months ahead of where you are? What have been his biggest lessons from scaling internationally so fast?

5.) How does Steven think about and approach investor selection? What can founders really do to leverage their investor base and get the most value from them? How does Steven think about the incredibly high CACs of the core channels today? What must founders in the world of consumer do to acquire customers more efficiently?

Items Mentioned In Today’s Show:

Steven’s Fave Book: Blitzscaling: The Lightning-Fast Path to Building Massively Valuable Companies

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

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

Jun 24, 2019

Bill Gurley is a General Partner @ Benchmark Capital, one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many many more. As for Bill, widely recognised as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix and Zillow. Prior to Benchmark, Bill was a partner with Hummer Winblad Venture Partners. Before entering venture, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at CS First Boston where his research coverage included such companies as Dell, Compaq, and Microsoft, and he was the lead analyst on the Amazon IPO.

In Today’s Episode You Will Learn:

1.) How did Bill make his way into the world of VC from Credit Suisse and come to be GP at one of the world's leading funds in the form of Benchmark? What were Bill's biggest takeaways from seeing the boom and bust of the dot com? How did that impact Bill's investment mentality today?

2.) Why does Bill believe that one of the biggest challenges today is the abundance of capital? Subsequently, does Bill agree with Peter Fenton statement, "never turn down a deal based on the valuation it is a mental trap"? How does Bill assess his own price sensitivity? What was his learning here in meeting Larry and Serge early on with Google?

3.) How does Bill think about and approach market sizing today? How important is it to him when analysing an investment? Where does Bill believe a lot of managers make mistakes when assessing market sizing today? What was his big lesson here with Uber? How does Bill think about and evaluate market creation and market expansion plays?

4.) Bill has spent over 3,000 hours on some of the most famed boards of the last decade, how has Bill seen his style of board membership change over the last 10 years? What advice would you give to someone who has just joined their first board? How does Bill think about time allocation across the portfolio? What is the right ratio?

5.) How does Bill and Benchmark approach the element of partner selection today? What are the 5 core things that Bill looks for when adding to the partnership? What have Benchmark done that have allowed them to be so successful in generational transition? Why is an equal partnership so transformative when it comes to generational transition?

Items Mentioned In Today’s Show:

Bill’s Fave Book: Complexity: The Emerging Science at the Edge of Order and Chaos

Bill’s Most Recent Investment: Good Eggs

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

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

Jun 21, 2019

Justin Kan is the Founder and CEO @ Atrium, the startup providing a full-service corporate law firm that uses modern technology to give startups a legal experience that is fast, transparent, and price-predictable. To date, Justin has raised over $75m in funding from some of the best in the business including Founders Fund, a16z, First Round, General Catalyst, Thrive, Initialized and more. Prior to founding Atrium, Justin was a Partner @ Y Combinator, the globally renowned accelerator and the birthplace of some of today's largest startups. Before that Justin was the Co-Founder @ Twitch, the world’s leading video platform and community for gamers which was acquired by Amazon for $970m. If that was not enough, Justin is also a prolific angel investor with investments in the likes of Cruise Automation, Rippling, Zenefits, Triplebyte and more.

In Today’s Episode You Will Learn:

1.) How Justin made his way into the world of startups and YC? How that led to the founding of Justin.TV, later Twitch? What was that a-ha moment for Atrium?

2.) Why did Justin feel that being an investor full time was not for him? How does Justin think about and approach the learning process as a founder? What advice does Justin give to those who want to quit? What was it that made Justin embrace the series of self-improvement habits he now practices?

3.) What does Justin mean when he says, "attaching yourself to outcomes will only cause your own suffering”? How does Justin think about and advise founders when it comes to burnout? How does Justin feel about the "crushing it" culture in tech? What can we do to normalise vulnerability? What were Justin's biggest takeaways from "The Score takes Care of Itself"?

4.) What have been Justin's experiences with therapy? How does he advise founders thinking of engaging with therapists? What have been his biggest lessons that drive success in therapy? How does Justin look to show authenticity through positivity? What does that really mean?

5.) What have been Justin's biggest takeaways from "The 15 Commitments of Conscious Leadership"? What are the core principles? What is required to roll out these values and principles within an organisation? What are the fundamental challenges to successfully roll this out on a large scale within your company?

Items Mentioned In Today’s Show:

Justin’s Fave Book: The 15 Commitments of Conscious Leadership

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

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

Jun 17, 2019

Jonathan Hsu is Co-Founder & General Partner @ Tribe Capital, one of Silicon Valley's newest funds on the block being founded by Jonathan, Arjun Sethi and Ted Maidenberg. To date, Tribe has invested in the likes of Carta, Cover, Mode Analytics, Prodigy and SFOX. As for Jonathan, before founding Tribe he was a Partner @ Social Capital where he utilized data and technology to augment sourcing, evaluation of investment opportunities and the management and value add for portfolio companies. Before that he led the creation of the analytics and data science team at Facebook, including leading the hiring of 200 of the world's leading data scientists and analysts.

In Today’s Episode You Will Learn:

1.) How Jonathan made his way from leading 200 data scientists at Facebook to the world of venture and founding his own firm in the form of Tribe Capital today?

2.) If we structure VC simplistically, there are 4 core components:

  • Sourcing: How does Jonathan think about the role of data in actively surfacing the best opportunities? that are the leading data fields that Jonathan would track? Why does Jonathan believe most early-stage firms are just using Linkedin Sales Navigator intelligently?
  • Evaluating: How does Jonathan think about the potential for data to really aid in the picking process? At what stage does this really become possible? How much data is required for data to evaluate opportunities?
  • Winning: Winning deals is seemingly a case of human relationships but how does Jonathan think intelligent data usage and benchmarking can actually help firms win the most competitive deals?
  • Value Add: How does Jonathan think about portfolio management with data? How does this differ from the more traditional "value add" that other VCs provide? Where are the common pitfalls Series A companies you work with face in not achieving product-market fit?

3.) Given the data-driven nature of the approach, does Jonathan think that there is an optimal portfolio construction? Why does Jonathan strongly believe that historical loss ratios are too high? Does data allow firms to really intelligently price these assets at the Series A and B? What are the challenges in pricing these assets so early?

4.) How does Jonathan think about reserve allocation? Why is data more critical than ever in the decision to re-invest or not? What are the leading data signals that Jonathan looks for when determining reserve allocation? Why does Jonathan think that so many firms go wrong in how they approach reserve management and distribution?

5.) Question from Henry Ward @ Carta: What does N of 1 markets mean to you Jonathan? Why are they so inherently attractive? How do pricing dynamics play out in markets that are N of 1? How does Jonathan think about defensibility when analysing opportunities today? Is anything truly defensible anymore?

Items Mentioned In Today’s Show:

Jonathan’s Fave Book: The Origins of Political Order: From Prehuman Times to the French Revolution

Jonathan’s Most Recent Investment: Carta

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

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

Jun 14, 2019

Brad Bao is the Co-Founder & CEO @ Lime, the startup that provides distribution of shared scooters, bikes and transit vehicles, with the aim to reduce dependence on personal automobiles for short distance transportation. To date they have raised over $775m in funding from the likes of Andreessen Horowitz, GV, IVP, Uber, Fifth Wall, GGV, Atomico and Bain Capital Ventures just to name a few. As for Brad, prior to founding Lime he was Managing Partner @ Kinzon Capital for close to 6 years and before that spent an incredible 8 years at Tencent in numerous different roles including VP of Business Development for Tencent Games and General manager for Tencent's US branch where he was responsible for Tencent's US operations.

In Today’s Episode You Will Learn:

1.) How Brad made his way into the world of technology with Tencent, how that led to the world of investing and then what was that a-ha moment for the founding of Lime? How did Brad's time with Tencent impact his operating mentality today with Lime?

2.) With significant levels of competition, how does Brad assess the competitive landscape today for micro mobility? Does Brad believe customer loyalty comes into play in the segment? Is capital itself a defensible moat in this market? Why is Brad adamant that it is important to spend $0 on marketing? What does this say about the product?

3.) How does Brad think about technological innovation within the space? Does it subscribe to Moore's law in the advancement of the core components? How does Brad think about inherent trade-offs that have to be made in product decisions? How does Brad think about prioritising for unit cost vs product superiority? Why can you not have it all?

4.) How does Brad think about launching new cities? What does it take to win in those geographies? What are all the necessary parts to setup when entering a new location? What is the biggest determinant of a location success? Density? Maturity?

5.) Brad has assembled a truly world-class exec team, what does Brad think it takes to attract truly A* talent? When should founders really start to think about building out their own exec team? What does Brad believe it is that makes his partnership with Toby Sun work so well? What have been his learnings from the development of that relationship?

Items Mentioned In Today’s Show:

Brad’s Fave Book: Good To Great by Jim Collins

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

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

Jun 10, 2019

Scott Kupor is Managing Partner @ Andreessen Horowitz, one of the world's most renowned venture funds with a portfolio including the likes of Facebook, Airbnb, Github, Lyft, Coinbase, Slack and many more. As for Scott, he has been with the firm since its inception in 2009 and has overseen its rapid growth, from three employees to 150+ and from $300 million in assets under management to more than $7 billion today. Before a16z, Scott was a VP @ HP where he managed a $1.5 billion (1,300 person) global support organization for HP Software product portfolio. Scott joined HP as a result of his prior company Opsware, being acquired, where he served as a Senior VP across numerous roles across an incredible 8-year journey. 

In Today’s Episode You Will Learn:

1.) How Scott made his way from the world of law to startups to being Managing Partner at one of the world's most renowned venture firms in the form of a16z?

2.) How did seeing the boom and bust of the dot com bubble and 2008 impact Scott's operating mindset today? Why does he argue that those times are so drastically different to today? How do public markets fundamentally diffferent? How do teams approach to capital efficiency and scaling differ significantly?

3.) What does Scott believe entrepreneurs get most wrong when pitching VCs? Why does Scott argue that product is not the core when pitching VCs? Does Scott agree with Fred @ Okta in weighing it: 70% market, 20% team, 10% product? What is Scott's weighting? Why does Scott believe that the compression of fundraising timelines is a problem? What pitch sticks out to Scott above all others? What made it so memorable?

4.) How does Scott advise founders on determining the right amount to raise for? Does Scott believe that founders should ask for a specific number or a range? Why does Scott believe raising for "runway" is the wrong mindset? Does Scott believe that most bridges are bridges to nowhere? If so, what is the next step? How does one relay that information to the founders?

5.) What have been some of Scott's biggest learnings from building the firm with Marc and Ben? What does Scott believe have been the biggest inflexion points in the public status of a16z? What have been the biggest challenges for Scott in the scaling of the firm? How does he foresee that changing in the future?

Items Mentioned In Today’s Show:

Scott’s Fave Book: Master of the Senate: The Years of Lyndon Johnson

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

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

Jun 7, 2019

Zach Perret is the Founder & CEO @ Plaid, the startup providing the easiest way for users to connect their bank accounts to an app whether it be transactions, identity or authentication. To date, Zach has raised over $300m with Plaid from some of the best in the business including Mary Meeker, Index Ventures, Andreessen Horowitz, Felicis, Spark and Homebrew, just to name a few. As for Zach, as CEO he has scaled Plaid to today with over 300 employees, 3 international offices and over 10Bn transactions analysed. Prior to founding Plaid, Zach was a consultant @ Bain.

In Today’s Episode You Will Learn:

1.) How Zach made his way into the world of startups from consulting at Bain and what led to the founding of Plaid and the mission to unlock consumer finance? What advice would Zach give to emerging grads today, questioning whether to join or start a startup?

2.) What does great leadership and CEOship look like to Zach? How has Zach seen himself evolve and develop as a leader over the last few years? How does Zach think about prioritisation? How does Zach determine what to say yes vs what to say no to? What has Zach found the most challenging in scaling as a CEO? What has he done to mitigate this?

3.) How does Zach think about constructing the optimal recruitment process? What have been some of Zach's biggest lessons in what it takes to really recruit world-class talent? What does Zach mean when he says, "you have to hire for spikes"? How does Zach manage the tension of keeping the high-quality bar whilst also sustaining the very steep growth curve?

4.) Plaid recently raised $275m, how does Zach think about capital efficiency with Plaid today? How does Zach determine when is the right time to transition from the mindset of lean and iteration to raising a war chest and going for the home run? What is Zach's biggest advice to founders when it comes to investor selection? Is it possible for the investor and the founder to be "friends"?

5.) When assessing the fintech landscape today, what is Zach most excited to see develop over the next 12-18 months? How are we seeing much larger incumbents like Goldman innovate in the proliferated world of fintech startups? How does the US view the fintech innovation that has occurred in the UK? What does this mean for US fintechs?

Items Mentioned In Today’s Show:

Zach’s Fave Book: Hard Drive: Bill Gates and the Making of the Microsoft Empire

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

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

Jun 3, 2019

Zach Coelius is Managing Partner @ Coelius Capital and in his own words, "a pretty eclectic investor who loves to see just about any deal". To date, Zach has made investments in the likes of mParticle, Cruise Automation, Branch Metrics, SkySafe, ProsperWorks and more. In addition, Zach is or has been an advisor to LiveRamp, Hellosign, Art19, Loom.ai, Survata and StartGrid just to name a few. Prior to his investing career, Zach was CEO @ Triggit, an online adtech company which he raised over $18m for and was ultimately acquired in 2015. If that was not enough, Zach is also a Senior Advisor to McKinsey & Co.

In Today’s Episode You Will Learn:

1.) How Zach made his way from the world of operating and adtech to investing and advising startups today? When does Zach feel the ecosystem really started to take him seriously as an investor? What did Zach learn from being in the adtech space that he has applied to his investing today?

2.) The Future of Venture: Naval has previously said we will see "the unbundling of VC", does Zach agree with this view? Why does Zach feel we are seeing both the bundling and the unbundling of venture platforms? What unique challenges does this pose for both sides of the equation? How should entrepreneurs evaluate the different options, bundled vs unbundled?

3.) Portfolio Construction: Why does Zach believe that portfolio construction is fundamentally inefficient? What 2 core areas of venture does portfolio construction cause issues for? When does Zach view to be the ideal insertion point if optimising for absolute returns and not following portfolio construction?

4.) Reserve Allocation and Pricing: Why does Zach think that the current mechanism for reserve allocation is broken? Why is it a fundamentally bias process? What does the optimal investment decision-making process look like to Zach? How does Zach think about the asymmetric information that is gained from being early into a company? How can investors really use it to their advantage? Why do they not?

5.) Why does Zach compare being an entrepreneur to being a gladiator and a rocketship? Why does Alex believe the transition from space articulation to product articulation is the most important thing an entrepreneur can do? What is the true sign of this transition in customer interactions? Where do many entrepreneurs make mistakes here?

Items Mentioned In Today’s Show:

Zach’s Fave Book: The Snowball: Warren Buffett and the Business of Life

Zach’s Most Recent Investment: Mud\Wtr

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

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

May 31, 2019

Kulveer Taggar is the Founder & CEO @ Zeus Living, the startup providing a home of your own for business travel with smartly furnished homes for extended stays. To date, Kul has raised over $14m in VC funding from some dear friends of the show in the form of Garry and Alexis @ Initialized, James and Pete @ NFX, Mike @ Floodgate, Y Combinator, GV and Naval Ravikant just to name a few. Prior to Zeus, Kul co-founded Auctomatic alongside Stripe's Patrick Collison, they ultimately sold the company for $5m. Before that, Kul co-founded Bosco, alongside former 20VC guest, Monzo's Tom Blomfield, they raised seed funding from YC before moving to the states to start Auctomatic. If that wasn't enough, Kul has also made several angel investments in the likes of Boom, Airhelp, Meetings.io and more.

In Today’s Episode You Will Learn:

1.) How Kul made his way from Oxford University to being at the centre of one of tech's most powerful hubs of YC and then with the founding of Zeus? What were Kul's biggest takeaways from his first 2 startups? How did that impact his operating mentality?

2.) What did the idea generation process look like for Kul with Zeus? How was James Currier @ NFX so foundational helping here? Why does Kul believe that the idea "really is everything" today? Why does Kul believe that customer acquisition channels are a core part of the product that must be considered from Day 1?

3.) Before hitting on Zeus, Kul and the team had many ideas, what did that idea validation process look like? How did Kul keep morale high in the team when continuously trying and stopping work on new projects? How does Kul think you can use culture as a superpower? As a leader, how can you be both vulnerable and strong at the same time?

4.) Kul has previously said that "tech-enabled businesses are just much harder than pure software plays". Why is that? What makes them so much more challenging? How do the required skills to be successful change when moving from pure software to tech-enabled? What single question remains the most important to ask when innovating in either?

5.) VCs are not so used to such operationally heavy businesses so how did Kul find the fundraising process? Why does Kul advocate that all founders should speak to investors and A/B test their idea before starting work on it? How did investors differ when comparing SF vs NYC? How did the messaging have to change? What was the most common pushback or concern? What have Initialized done to have such a foundational impact? What makes Garry such a special investor to have on board?

Items Mentioned In Today’s Show:

Kul’s Fave Book: How The Mind Works by Steven Pinker

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

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

May 27, 2019

Geoff Ralston is President @ Y Combinator, the world's leading accelerator with a portfolio that includes the likes of Stripe, Airbnb, Dropbox, Coinbase, Instacart, DoorDash, Flexport and so many more. As for Geoff, he started his career running engineering at Four11, where he built RocketMail, which in 1997 became Yahoo! Mail. At Yahoo! Geoff worked in engineering, then ran a business unit, then became Chief Product Officer. After Yahoo! he was CEO of Lala, which was acquired in 2009 by Apple. Post Lala, Geoff then co-founded the world’s first educational technology accelerator, Imagine K12 which funded dozens of edtech companies including ClassDojo, Remind, and Panorama Education. Imagine K12 merged with YC in 2016.

In Today’s Episode You Will Learn:

1.) How Geoff made his way into the world of technology and startups, came to found Imagine K12 and how that led to becoming President @ Y Combinator today?

2.) What were Geoff's biggest takeaways from seeing the boom and bust of the macro environment in the dot com and 2008? How did those times impact both his operating and investing mentality? Why does Geoff believe 2000 was "purifying"? Why can the same not be said for 2008? How was 2008 so different?

3.) Frederic Kerrest @ Okta said: "it is 70% market, 20% team and 10% product", would Geoff agree with this weighting? How has his weighting changed over time? YC has "10 Minute Meetings", how can YC really determine whether someone is investable in 10 mins? How does Geoff think about the hailed VC term, "pattern matching"? Why does Geoff believe you lose as an investor if you fall back on "profiles"?

4.) Geoff has worked with 100s of founders in the idea validation stage, how does Geoff know when a founder has the right idea? How does Geoff think about the balance between mission and vision but then also being realistic about when something is not working? When do you quit? Why is the decision internal not external? What is the most important perspective any investor can give a founder?

5.) How does Geoff think about the coined term "product-market fit" and how does he analyse it in terms of retention and growth? If they have some signs of it, how should founders think about when is the right time to raise their first round? How does Geoff think about the benefits for founders of convertibles and now SAFE's? What does Geoff believe will be the future of legal round mechanics?

Items Mentioned In Today’s Show:

Geoff’s Fave Book: Titan: The Life of John D. Rockefeller

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

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

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

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