20VC: Fiverr CEO: ‘If You’re Not Adapting to AI, F* You. You’re Done | Why "Time to Copy" is the Most Important Metric in Startups Today | Why 99% of AI Companies Today Will Die | Why Governments Will Take Control of AI with Micha Kauffman

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.

23 Huhti 201828min

Marco Zappacosta is the Founder & CEO @ Thumbtack, the startup that allows you to find local professionals for pretty much anything. To date, Thumbtack has raised over $270m in funding from some of the very best including Sequoia Capital, CapitalG (Google Growth), Ali and Hadi Partovi, Scott and Cyan Banister and Jason Calacanis. Due to Marco's incredible success scaling Thumbtack to helping millions of Americans today, he has been recognized by Forbes as 30 under 30 and Thumbtack was recently acknowledged as one of GlassDoor’s best places to work. CLICK TO PLAY CLICK TO LISTEN ON ITUNES In Today’s Episode You Will Learn: 1.) How Marco made his way into the world of startups and came to create one of the most prominent marketplaces of the day in Thumbtack? 2.) What does Marco mean when he says "founders must treat board members as employees"? How does Marco view the optimal structure for a board meeting? What are the core elements that founders must takeaway? Where do most first time founders go wrong with board management? 3.) Thumbtack has raised over $250m in VC funding, how can one look to achieve both operational efficiency and capital efficiency with such large injections of capital? What is core to maintaining this sense of frugality despite such large investments? How does Marco think about when is the right time to raise that warchest round? 4.) How does Marco suggest that marketplace founders can entice the supply side in the early days? How has Marco seen his supply-side acquisition change and develop with time? What has worked and what has not? Does Marco agree with Leah Busque that in marketplace, the NPS for one side will always be down? Items Mentioned In Today’s Show: Marco’s Fave Book: The Wizard and The Prophet As always you can follow Harry, The Twenty Minute VC and Marco 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.

20 Huhti 201828min

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.

16 Huhti 201824min

Paul Hsiao is a Founding Partner @ Canvas Ventures, one of Silicon Valley's leading and newer entrants to the Series A scene. At Canvas, Paul has made investments in the likes of Everwise, Fluxx Labs, Roofstock, Thrive Global, Transfix, and Zola. Before founding Canvas, Paul was a partner at NEA, where he led an early-stage investment in Houzz, as well as, had the privilege of helping eight companies go public on the NYSE or NASDAQ and seventeen companies with successful M&A exits during his 10-year tenure with the firm. Prior to VC, Paul was an entrepreneur with the founding of Mazu Networks, a pioneer in network security that was acquired by Riverbed Technologies. In Today’s Episode You Will Learn: 1.) How Paul made his way into the world of VC with NEA and got Scott Sandell as his first mentor in VC? 2.) Question from Oren Zeev: Having been a partner at both, how does Paul compare the culture and strategy of two such differing firms of Canvas vs NEA? How does Paul's thinking on exit expectations and requirements change with the change of fund? How does a smaller fund fundamentally change the way you think about investing? 3.) What does Paul believe are the 5 fundamentals of building and scaling a successful marketplace? Why does Paul believe that it is the supply side that tells you if your marketplace is or is not working? Why does Paul believe stubbornness is good in marketplace founders? 4.) Why does Paul believe that raising $100m is critical for new companies if they want to go big? What does this mean for capital efficiency? What does this mean for ownership with multiple dilutive rounds impacting investor returns? How should founders then think about winning the "capital arms race"? What are the exceptions to these rules? 5.) Female founders receive 2.19% of VC funding, however, Paul has many more female founders in portfolio than the industry. Why does Paul think this is? What would Paul like to see change in the distribution of VC funds? What is the required steps to make this happen? Items Mentioned In Today’s Show: Paul’s Fave Book: The Innovator's Dilemma Paul’s Most Recent Investment: Thrive Global, Roofstock As always you can follow Harry, The Twenty Minute VC and Paul 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.

9 Huhti 201823min

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.

6 Huhti 201832min

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.

2 Huhti 201831min

Rachel Drori is the Founder & CEO @ Daily Harvest, the direct-to-consumer brand that delivers real, unprocessed, unrefined foods in the most convenient format possible: frozen. To date, they have raised over $43m in funding from the likes of former guest Alex Taussig @ Lightspeed, Collaborative Fund and future 20VC guest Beth Ferreira who sits on the board. As for Rachel, prior to starting Daily Harvest, Rachel harnessed her skills as a customer-centric marketing executive, leading teams at Gilt Groupe, American Express, and Four Seasons Hotels and Resorts. In Today’s Episode You Will Learn: 1.) How Rachel made her way from the corporate world of American Express and The Four Seasons to founding Daily harvest, looking to change the eating habits of millions? 2.) Why did Rachel decide to deliberately raise small Seed and Series A rounds? What does Rachel believe these capital constraints allow companies in the early days? How did Rachel prioritize where to spend and where not to? How would Rachel advise emerging startup founders when it comes to capital efficiency today? 3.) Rachel recently raised $43m Series B, how did Rachel see the rounds differ from round to round? Why does Rachel believe it is imperative to VC date before the fundraising process begins? Why was Rachel's Series A very unconventional in the modern world of fundraising? What did Rachel look for most in the investors she chose from round to round? How is that different considering her single founder status? 4.) Question from Alex Taussig: How has Rachel seen the NYC ecosystem develop and evolve since the founding of Daily Harvest? Would Rachel agree that there remains a lack of early stage conviction investors in NYC? What are NYC's biggest strengths and then biggest weaknesses? 5.) Rachel has said before, "fake it till you make it" when was the last time Rachel did this and what was the outcome? Rachel also said previously, "ask for forgiveness not permission", when was the most recent occassion of this and what did it result in? Items Mentioned In Today’s Show: Rachel’s Fave Book: Deep Nutrition: Why Your Genes Need Traditional Food: Volume 1 As always you can follow Harry, The Twenty Minute VC and Rachel 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.

30 Maalis 201824min

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.

26 Maalis 201828min