The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Chris Olsen is the Founding Partner @ Drive Capital, the venture firm that believes the Midwest is the opportunity of our lifetime with more entrepreneurs building billion-dollar companies in the Midwest than in the last 50 years combined. Since inception in 2012, Drive have built an exceptional portfolio including the likes of Duolingo, FarmLogs, LeadPages and Udacity. As for Chris, prior to founding Drive he was a Partner @ Sequoia Capital on the West Coast where he learned the craft from some of the very best in the business. Before that he spent time at both TCV and UBS. In Today's Episode You Will Learn: 1.) How Chris came to found the largest venture fund in the midwest, Drive, from being a Partner @ Sequoia Capital and learning the craft of venture there? 2.) Why does Chris believe that the biggest trend we will live through is the decentralisation away from Silicon Valley? What are the essential ingredients an ecosystem requires in order to foster this thriving tech hub? What does Chris believe it is fundamentally essential for companies to be in close proximity to? 3.) How does the lack of venture funds in the Midwest affect Chris' views on pricing? Would Chris agree with Peter Fenton, "never turn down a company based on valuation, it is a mental trap"? How does Chris look to differentiate between expensive and too expensive? 4.) How does Chris think about reserve allocation with Drive? What framework does Drive adopt to determine where to allocate reserve dollars? How does the shortage of follow-on investors in the midwest impact Chris' approach to follow on financing? What level does a company need to be in order to attract attention from larger growth funds? Items Mentioned In Today's Show: Chris' Fave Book: The Old Man and The Sea Chris' Most Recent Investment: Duolingo As always you can follow Harry, The Twenty Minute VC and Chris on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm. Simply head over to Cooley.com or you can check them out at Cooleygo.com.

Marco Zappacosta, Founder & CEO of Thumbtack, discusses the core elements of board meetings, raising $250m from Sequoia, and winning supply side acquisition for marketplace success.

Zal Bilimoria is Founding Partner @ Refactor Capital, one of Silicon Valley's newest entrants to the early stage scene with a $50m fund looking to back founders solving fundamental human problems. Prior to co-founding Refactor, Zal was a Partner @ a16z where he co-led investments in Omada Health, Branch.co, AltSchool, Honor, and more, while helping to launch the firm's Bio Fund. Before becoming an investor, Zal spent 10 years as a PM at Microsoft, Google, Netflix, and LinkedIn. He worked on emerging markets for Windows, became one of the first monetization team members at YouTube, and then became the 1st Head of Mobile at Netflix and helped start the Sales Solutions business at LinkedIn. In Today's Episode You Will Learn: 1.) How Zal made his way into the world of VC with a16z from the very corporate worlds of Microsoft, Google, Netflix and LinkedIn? 2.) What were Zal's 3 biggest learnings from seeing the internal processes and scaling of a16z? How does a16z use NPS in such a compelling way that it automatically improves founder treatment and interaction within the firm? What was it about a16z that led Zal to believe being insanely curious is the biggest skill of an investor? 3.) What are the signs and leading indicators that a scientist has the mental plasticity and ability to translate into a CEO and business leader? What are the biggest challenges as a VC in assessing whether this plasticity is present? Why does David believe that the very best founders are looking to solve "fundamental human problems"? 4.) Over the last few years we have seen an explosion of deep tech capital, Elad Gil suggested this reminded him of the 2007 cleantech days, does Zal agree with this suggestion? How does Zal think about the common concern of having to carry companies for longer given the extended milestones to prove progress? 5.) Zal has said before his goal is "to build a seed firm to last among the 100s of others", what does Zal believe is crucial to this sustainability of fund and brand? How does Zal evaluate the insanely crowded seed market today? Items Mentioned In Today's Show: Zal's Fave Book: Seveneves Zal's Most Recent Investment: Solugen As always you can follow Harry, The Twenty Minute VC and Zal on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm. Simply head over to Cooley.com or you can check them out at Cooleygo.com.

Paul Hsiao, Founding Partner at Canvas Ventures and a prominent figure in Silicon Valley's venture capital scene, discusses his journey from biomedical engineering to investing. He shares the five fundamentals for scaling successful marketplaces, emphasizing the critical role of supply dynamics. Paul also stresses why aspiring startups should aim for $100 million raises to ensure substantial growth and addresses the nuances of investing strategies between Canvas and NEA. His insights are invaluable for understanding today’s funding landscape.

Darian Shirazi is the Founder & CEO @ Radius, the startup that provides you with not just data but truth allowing you to gain clarity to reach and convert your best B2B prospects. To date, Darian has raised over $105m in VC funding with Radius from some of the very best in the business including our friends at Founders Fund, 8VC, Salesforce Ventures and rockstars like Jared Leto and Charlie Songhurst. Prior to Radius, Darian has enjoyed roles such as first external engineering hire at Facebook and working on the "Sell Your Item" team at eBay. Darian has also made several angel investments in the likes of MessageMe, Sprig and Try.com just to name a few. In Today's Episode You Will Learn: 1.) How Darian made his way into the world of tech as Facebook's first ever intern at the age of 17 and how that led to the founding of Radius? 2.) According to Joe Lonsdale @ 8VC, "Darian is one of the most respected founders and CEOs in the valley". How does Darian define great CEOship? What have been the commonalities he has seen in the great leaders he has engaged with from Mark @ Facebook to Mark Pincus? 3.) How did Darian approach the fundraising strategy for the $85m he has raised with Radius? How does Darian believe that founders can test quickly whether an investor is truly interested? Why is it so important to be fundraise as fast as possible? If an investor could only provide Darian one thing, what would it be and wh? 4.) How does Darian respond to investors that suggest founders should not be actively angel investing, as Darian is? What operational benefits does Darian gain from angel investing? How does Darian think about angel portfolio construction and specialisation? How has Darian seen investor attitudes alter when it comes to capital efficiency? 5.) As an early Bitcoin miner, how does Darian evaluate the world of crypto today? Why does Darian believe BTC has reached escape velocity compared to other currencies? Why was Darian skeptical on Ethereum for so long? What are Ethereum's ongoing challenges? Why does Facebook have the chance to dominate the world of crypto? Items Mentioned In Today's Show: Darian's Fave Book: Sapiens As always you can follow Harry, The Twenty Minute VC and Darian on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm. Simply head over to Cooley.com or you can check them out at Cooleygo.com.

Jerry Chen is a Partner @ Greylock Partners, one of the world's most successful VC funds with prior investments in the likes of Facebook, Instagram, LinkedIn, AirBnB, Dropbox, AppDynamics, Coinbase and many more incredible companies. As for Jerry, Jerry invests in entrepreneurs building new enterprise SaaS applications and in all aspects of AI and cloud infrastructure. Jerry currently sits on the Board of Docker, Cato Networks, Gladly, Rhumbix, Spoke, and Blend. Prior to joining Greylock, Jerry was Vice President of Cloud and Application Services at VMware where he was part of the executive team that scaled the company from 250 to over 15,000 employees and $5B in revenue. Check out Jerry's recent writing on Risk: The Game of Strategic Investment here. CLICK TO PLAY CLICK TO LISTEN ON ITUNES In Today's Episode You Will Learn: 1.) How Jerry made his way into the world of VC with Greylock from being on the exec team at VMWare, responsible for their scaling from 250 to over 15,000 people? 2.) What does Jerry believe are the different frameworks for how investors should measure risk? Why does Jerry believe to be a good investor, one has to be an optimist? What does Jerry find the most challenging element of risk assessment? What types of risk can Jerry tolerate and which can he not in a potential investment? 3.) How does Jerry break the theme of risk down into 2 very different categories? How does one define "uncertainty" in an investment? How does this compare to "probability"? How does both "uncertainty and probability" alter when comparing differing sectors? Does Jerry think that current pricing takes fair account of both "uncertainty and probability"? 4.) What does Jerry mean when he says, "you have to have product go-to-market fit"? Why does Jerry believe that platforms shifts are fundamentally distribution model shifts? Where does Jerry see an inherent opportunity within these net new nodes of distribution shift? 5.) How does Jerry evaluate the SaaS world today of bottoms up or top down? Why does Jerry believe that if you are budget additive, bottoms up with small ACVs is the current strategy? What does this mean for those that are budget replacements, both in sales model and ACV? Items Mentioned In Today's Show: Jerry's Fave Book: Skin In The Game Jerry's Most Recent Investment: Blend As always you can follow Harry, The Twenty Minute VC and Jerry on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm. Simply head over to Cooley.com or you can check them out at Cooleygo.com.

Rachel Drori, Founder and CEO of Daily Harvest, shares her journey from the corporate world to revolutionizing food with her frozen, unprocessed brand. She discusses the strategy behind raising smaller funding rounds, emphasizing capital efficiency and its benefits during early growth. Rachel highlights the importance of 'VC dating' before fundraising and the lessons learned from each funding stage. She also delves into the bold risks of entrepreneurship, even balancing motherhood with business ambitions, and future innovations for healthy eating solutions.

James Loftus is Corporate Development Lead @ Square where he has made multiple acquisitions and investments including the likes of acquiring OrderAhead and investing in Eventbrite. Prior to Square, James was responsible for strategy, business development and operations at STX Digital. Before that James was a Partner @ Andreessen Horowitz where he led strategic coverage for the firm's 45+ consumer-facing portfolio, advising them on everything from capital raising to partnerships to M&A. Prior to VC with a16z, James was VP & Head of Corporate Development @ Yahoo and also spent time in the M&A team at Google. In Today's Episode You Will Learn: 1.) How James made his way into the world of corporate development and M&A with Andreessen and how that translated to leading Square's M&A efforts today? 2.) Why does James fundamentally disagree with the notion that "companies are bought and not sold"? What are the nuances behind the scenes that make this wrong? 3.) 514 VC backed exits in 2017, 499 were M&A, so how does James assess the M&A landscape at present? Is it now the undeniable leader in primary exit method? How does James believe we will see the M&A market evolve over the next year? Who are the new entrants? How will their entering effect both volume and pricing of M&A? 4.) How does James respond to Paul Graham's article titled "Don't Talk To Corp Dev"? How does James and Square think about operationalizing the tracking of companies in the landscape? When is the right time for startups to relationship build with corp dev? How does James most like to interact with VCs in the processes? What makes the best so good? 5.) Paul Graham has also called the process "grueling", would James agree with this? What does James do to minimise pain and friction both for startup and acquirer? How does product play a pivotal role in this "grueling" process? How should cor dev also be thinking about the emotional and sentimental elements of selling companies? Items Mentioned In Today's Show: James's Fave Book: A History Of The World In 10 1/2 Chapters James's Most Recent Investment: Eventbrite As always you can follow Harry, The Twenty Minute VC and James on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep! Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don't take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Dan Lewis is the Founder & CEO @ Convoy, the startup that really is the future of freight with trucking services powered by technology to drive reliability, efficiency and insights. To date they have raised over $80m in funding from some of the world's best-known investors and individuals including Y Combinator Continuity Fund, Greylock, Jeff Bezos, Marc Benioff, Drew Houston, Kevin Systrom and leading angels, Ali and Hadi Partovi. Before Convoy, Dan served as general manager of new shopping experiences at Amazon and spent time at Google and Microsoft in a number of logistics-related roles. In Today's Episode You Will Learn: 1.) How Daniel first fell in love with the logistics space as a little boy, made his move into the world of tech with Google and Microsoft and came to found Convoy? 2.) How does Dan truly define the differences between linear and non-linear businesses? Why does Dan believe that startup timing is like surfing? How must founders think about this through the different stages of the business? 3.) What was Dan's strategy for choosing the right investors and how did he think about board composition? How can investors be used to build customer trust? How does Dan analyze and look to enhance board chemistry? What was a time for Dan when he actively went against the advice of the board? How did that play out? 4.) Why did Dan accept so many investors at the seed round? What changed between rounds that made Dan want to go big with the $62m Series B? Does Dan agree with Reid Hoffman, "if you can raise the money, do"? Why did Dan choose YC Continuity Fund as the lead growth investor of choice? What were the benefits? 5.) Why does Dan believe that scaling the first initial customers is the hardest of all? Why does Dan believe that a culture of experimentation is key across functions? How does Dan think about his own scaling as CEO? How has he seen his role change with the growth of the firm? What have been the biggest challenges of this personal learning? Items Mentioned In Today's Show: Dan's Fave Book: The Stranger by Albert Camus As always you can follow Harry, The Twenty Minute VC and Dan on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep! Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don't take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Leah Busque is a General Partner @ Fuel Capital, one of Silicon Valley's leading seed funds with the most incredible portfolio including many previous 20VC guests Ryan @ Flexport, Florian @ Mesosphere, Alex @ Clearbit and Dan @ Convoy (episode Friday). As for Leah, prior to VC, she was a pioneer of the sharing economy with her founding of TaskRabbit, one of the leading online labor marketplaces in the US, raising over $37m in the process before their sale to IKEA last year. Due to this incredible success, Leah has been named to Fast Company's "100 Most Creative People in Business". In Today's Episode You Will Learn: 1.) How Leah made her way from sitting on the couch discussing dog food with her husband to founding TaskRabbit and how that translated into the world of VC today? 2.) How did Leah's time in operations affect: Question from Sean @ Shasta: the founders Leah backs and why she chooses them? Question from Craig @ Collaborative: the business models and unit economics Leah backs and why she backs them? 3.) Leah has said before that "authenticity and transparency between VC and founder are now table stakes", what more can be done to improve the VC product? How did Leah select the investors she worked with on TaskRabbit? How can founders truly determine "founder friendly" VCs? 4.) What have been Leah's biggest surprises on her move into the world of VC? What elements has Leah found most challenging? How has Leah looked to scale that learning curve? 5.) What does a successful marketplace look like? How does one know when is the right time to really scale a marketplace? What is the inflection point? How can marketplaces be efficient with their unit economics from day 1? How does one balance the NPS of the supply side with the NPS of the demand side? Items Mentioned In Today's Show: Leah's Fave Book: Founders at Work Leah's Most Recent Investment: Bark: Parental Control Phone Tracker App As always you can follow Harry, The Twenty Minute VC and Leah on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep! Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don't take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.