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

Sumeet Gajri is the Chief Strategy Officer @ Carta, the startup that helps companies and investors manage their cap tables, valuations, investments, and equity plans. Sumeet is largely responsible for all things fundraising and M&A and Carta have raised over $485m from a16z, USV, Thrive, Spark, K9, Lightspeed and Meritech to name a few. Sumeet is also Managing Partner @ Original Capital, where he has partnered with companies including Front, Tonal, Instabase, Everlywell and Cockroach Labs to name a few. Finally, Sumeet is also an LP in world-leading firms such as USV and Valar Ventures. In Today's Episode You Will Learn: 1.) How Sumeet made his first foray into the world of venture in NYC having grown up in Scotland? How that led to his move to operations with Carta? How his learnings from Carta led to his establishing Original Capital? 2.) How is Original Capital different from every other micro-fund? How does Sumeet approach portfolio construction with the fund? What is the optimal number in a portfolio? How does Sumeet think about loss ratio? What 3 criteria dos every new investment have to pass to make it into the portfolio? How does check size vary by deal? 3.) How does Sumeet invest in some of the best companies in between "official rounds"? What does this conversation look like with the founders? How does Sumeet analyse reserve allocations? What makes the right strategy? What are his capital concentration limits per company? How does Sumeet think about using SPVs effectively? 4.) Sumeet helps his companies fundraise a lot, what does the first step look like? How does he advise on investor selection? How does he advise on pipeline management? Should founders speak to investors when they are not raising? How open should they be in these meetings? What can founders do to catalyse the process? Where does Sumeet see many founders make mistakes? 5.) How does Sumeet think about distribution vs product? What can founders do to adopt a more distribution first mindset? What have been some of Sumeet's biggest lessons in turning Carta from a single product company to a multi-product company? Do companies have to own their own lines of distribution today? Items Mentioned In Today's Show: Sumeet's Fave Book: Howard Marks: The Value of Predictions As always you can follow Harry, The Twenty Minute VC and Sumeet on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

17 Tammi 202057min

Samir Kaul is a Founding Partner and Managing Director at Khosla Ventures, one of the valley's most renowned firms of the last decade with a portfolio including Square, Affirm, DoorDash, Impossible Foods and OpenDoor just to name a few. As for Samir, he led the firm's investment in Guardant Health, Impossible Foods, Nutanix [NASDAQ: NTNX], Oscar, among others. Prior to Khosla, Samir spent five years at Flagship Ventures where he started and invested in early-stage biotechnology companies, including Helicos Biosciences which went on to IPO. Samir was also founding CEO of Codon Devices and led the Arabidopsis Genome Initiative at Craig Venter's Institute for Genomic Research. In Today's Episode You Will Learn: 1.) How Samir made his way into the world of venture from the world of biotech and came to found one of the leading firms of the last decade? 2.) How did seeing the booms and busts of the last 2 decades impact Samir's investing mindset? Why does Samir think it is dangerous for a VC to have a "conservative mindset"? How does Samir analyse and think about upside maximisation when investing today? How does Samir think about when to sell your position and how to determine the right time? 3.) What does investment decision-making look like at Khosla? What are the criteria that re-investments are made upon? Why does Samir believe that pro-rata is a kop out? Which should be the core questions that determine whether to double down or not? How does Samir and the partnership think about time allocation across the portfolio? 4.) How does Samir approach the exercise of market sizing? Why does Samir never want to take a risk when it comes to market? Why does Samir want to maximise his risk when it comes to technological risk? How does Samir think through having to carry these deep tech companies for longer? What were his learnings from the clean tech days on this? 5.) How would Samir analyse his own price sensitivity today? What was his most formative inflexion moment as an investor? What did he learn from it? From a people side, who had the biggest impact on Samir as an investor? What were the core elements he learned from them? How does Samir deal with the element of self-doubt? How does he get through those moments? Items Mentioned In Today's Show: Samir's Fave Book: Start Something That Matters Samir's Most Recent Investment: Lightship: Direct to Patient Clinical Trials As always you can follow Harry, The Twenty Minute VC and Samir on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

13 Tammi 202037min

Kurt Rathmann is the Founder & CEO @ ScaleFactor, the startup providing an automated bookkeeping solution at its core, bringing all of your company's important financial information into one place. To date, Kurt has raised over $105m with ScaleFactor from the likes of Byron Deeter @ Bessemer, Coatue, Canaan Partners, Stripes Group and Firebrand to name a few. As Michael @ Coatue told me before the show, there is no way Kurt was not going to be the founder of a bookkeeping company given his background. Prior to ScaleFacotr, Kurt was the CFO of KNS Communications and a Senior Audit Professional @ KPMG. In Today's Episode You Will Learn: 1.) How did Kurt make his way into the world of startups and come to found the gamechanger for bookkeeping in the form of ScaleFactor? Does Kurt believe that Founders do need to be mission-driven or can founding a company be a more analytical exercise? 2.) How did it come to be that Kurt raised 3 separate funding rounds and over $105m in just 13 months? How does Kurt feel about the saying, "when there is money on the table, take it"? Having had his B and C pre-empted, how does Kurt feel about the rise of pre-emptive rounds today? How did Kurt approach the mental challenge of transitioning from resource-starved to relative resource abundance? Was that tough to do? 3.) What is Kurt's biggest advice to founders when it comes to investor selection? What does Kurt believe are the 5 things that VCs can do to add value? Why does Kurt believe it is the responsibility of the founder to extract that value from the VC? What can founders do to really get the most out of their investors? What has Kurt found to be the biggest value from his cap table? Where do founders think VCs add value but they do not? 4.) What are some very unique and deliberate things that Kurt does to create an amazing culture at ScaleFactor? How does he advise on creating great energy in the office itself? How does Kurt think about retaining that core ethos with the expansion to multiple offices? What have been some of the biggest challenges in scaling communications internally? 5.) Does Kurt believe that being outside of a core tech hub severely limits his ability to hire the best talent? What do founders outside of these hubs need to very strategically do? How does being outside of a core hub also impact how Kurt thinks founders need to approach fundraising? What specifically can they do to increase their odds? Items Mentioned In Today's Show: Kurt's Fave Book: The Empowered Challenger Playbook: How Brands Can Change the Game, Steal Market Share, and Topple Giants As always you can follow Harry, The Twenty Minute VC and Kurt on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

10 Tammi 202035min

Gaurav Jain is Co-Founder & Managing Partner @ Afore Capital, one of the west coast's leading pre-seed funds with a $124M fund focused purely on pre-seed. To date, they have backed the likes of Petal, BetterUp, BenchSci and Modern Health to name a few. Prior to co-founding Afore, Gaurav was a Principal @ Founder Collective where he was directly involved with some incredible companies including Cruise (Acq. by General Motors for $1B+), Periscope (acq. by Twitter), Airtable and Dia & Co. Before venture, Gaurav spent time in operations both at Google as one of the first engineers for Android and then also founding his own company, Polar, a leading mobile solutions provider with $10m in funding. In Today's Episode You Will Learn: 1.) How Gaurav made his way into the world of venture with Founder Collective and how that led to the realisation that Afore needed to exist in the funding landscape? What were the 3 biggest takeaways for Gaurav from his time at Founder Collective? 2.) Why does Gaurav believe now is the hardest time in the last decade to raise your first institutional round of funding? What is driving these capital reductions at pre-seed? How does Gaurav assess the rise of operator funds and super angels we have seen in the last 5 years? How does Gaurav advise founders on investor selection at pre-seed? 3.) What does Gaurav make of large multi-stage funds entering into pre-seed? Why does Gaurav strongly believe that you cannot apply the same financing product to a different market? Does this mean the multi-stage funds will revert back to later stages? 4.) How is Gaurav seeing Series A funds behaving? Why are they more aggressive now than ever before? What does Gaurav make of the rise of pre-emptive rounds? How does he advise founders on pre-emptive rounds? 5.) How does Gaurav think about portfolio construction today with Afore? What is the right level of diversification across the portfolio to be sufficiently diversified at pre-seed? How does Gaurav think about reserve allocation today? How does the decision-making process compare when comparing initial to re-investment decision? Items Mentioned In Today's Show: Gaurav's Fave Book: Trillion-Dollar Coach: The Leadership Handbook of Silicon Valley's Bill Campbell Gaurav's Most Recent Investment: Modern Health As always you can follow Harry, The Twenty Minute VC and Gaurav on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

6 Tammi 202039min

Rahul Vohra is the Founder and CEO @ Superhuman, the fastest email experience in the world. Fun fact, users get through their inbox twice as fast — and many see Inbox Zero for the first time in years! To date, they have raised funds from our friends at Boldstart, First Round, John Collison, Sam Altman, Wayne Chang, Mike Ghaffery and Yes VC just to name a few. Previously, Rahul founded Rapportive, the first Gmail plugin to scale to millions of users. Rapportive was ultimately acquired by LinkedIn. In Today's Episode You Will Learn: 1.) How did Rahul make his way into the world of startups with the founding of Rapportive and how did that transition to changing the world of email with Superhuman? 2.) What does Rahul mean when he says, "you can reverse engineer a process to get to product-market fit"? What does Rahul believe is the defining metric which determines your "product-market fit score"? What is Julie Supan's framework? How did Dropbox and Airbnb use it to increase their product-market fit? How can founders implement it into their process? 3.) What can founders do to expand the customer base to include users that currently are "somewhat disappointed"? What are the right questions to ask? What do we do with this feedback? How do we further segment the user base? Why should we "disregard the users whereby the primary benefit of the product does not resonate"? 4.) How does Rahul approach product roadmap and prioritisation? How can founders ensure that continuous tracking and user feedback is engrained within the organisation? What tools does Rahul do to monitor and capture this? What are some of Rahul's biggest lessons from going through this painstaking process stage by stage? 5.) Finally on fundraising, what does Rahul mean when he says, "always be raising but never be actively raising"? What are the benefits of this? How can founders transition catch up coffee into fundraising subtly? How does Rahul feel about party rounds? What are the pros? What are the downsides? How does Rahul advise founders here? Items Mentioned In Today's Show: Rahul's Fave Book: The Art of Game Design As always you can follow Harry, The Twenty Minute VC and Rahul on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

3 Tammi 202041min

Rob Salvagno is VP of Corporate Development and Cisco Investments at Cisco, where he is responsible for leading all M&A efforts as well as managing Cisco's strategic venture capital which invests hundreds of millions of dollars annually. At Cisco, Rob led the $1.2 billion acquisition of Meraki, one of the most successful platform acquisitions in Cisco's history, and the $3.7 billion acquisition of AppDynamics, cementing Cisco's place in the business intelligence, analytics and IT operations market. Most recently, Rob engineered the $2.3 billion acquisition of Duo, the leading provider of unified access security and multi-factor authentication delivered through the cloud. Prior to the world of M&A, Rob was a technology investment banker at Donaldson, Lufkin & Jenrette. In Today's Episode You Will Learn: 1.) How Rob made his way from investment banking to leading the M&A and venture activity for one of the world's largest tech players of the last decade? 2.) How do M&A teams like to get to know startups that they could invest in or acquire? How does Rob like to work with the venture ecosystem? How does Rob think on Paul Graham's comment of "do not talk to corp dev"? What are the nuances here? How does it differ for consumer vs enterprise? 3.) How does Rob define true success when it comes to M&A evaluation? Should corp dev be strategy first or transaction first? What have been Rob's biggest lessons on successful integration? Where do so many go wrong with integration post M&A? What questions can be asked ahead of time to know if integration and culture will be a fit? 4.) How does Rob reflect on his own price sensitivity today? How does Rob feel about the multiples enterprise companies are currently trading at? What have Rob's most successful acquisitions taught him about price and price sensitivity? How does Rob deal with the inherent conflict of investing and also acquiring companies? How does he communicate that to the companies he invests in? 5.) What does the acquisition-decision making process look like at Cisco? How does it differ on a deal by deal basis? What do Cisco do to allow them to move so much faster than any other M&A teams? What have been Rob's lessons on the importance of speed in winning the best transactions? Items Mentioned In Today's Show: Rob's Fave Book: The Poisonwood Bible Rob's Most Recent Acquisitions: CloudCherry, Voicea As always you can follow Harry, The Twenty Minute VC and Rob on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

30 Joulu 201945min

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 Harry, The Twenty Minute VC and Bill on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

23 Joulu 201934min

Brandon Deer is VP of Operations & Strategy @ UiPath, one of the world's fastest-growing companies providing a complete software platform to help organizations efficiently automate business processes through robotic process automation. To date, UiPath has raised over $977m in funding from some of the best in the world including Sequoia, Accel, Meritech, IVP, CapitalG, Kleiner Perkins, Coatue and more. As for Brandon, prior to UiPath he spent 4 years as Vice President @ OpenView Partners where he made investments in Expensify, Logz.io, VTS and Pipefy to name a couple. Before OpenView, Brandon spent close to 4 years at Intuit in Strategy and Business Development. In Today's Episode You Will Learn: 1.) How Brandon made his way from being a rising star in the world of venture with Openview to leading one of the fastest-growing companies in history in UiPath? What has been the most surprising element in making the transition from investor to operator? 2.) How does Brandon think about decision-making today? How does he determine what to spend time on vs what to delegate? What does he mean when he says, "you have to think whether it is rubber or crystal?" How does that ultimately guide decision-making? 3.) What does the UiPath software actually do? What is the relationship between RPA and AI? Where do they differ? Where do they intersect? Recently, RPA has seen a meteoric rise, is this sustainable over the long term? How does Brandon respond to the suggestion that RPA is replacing human jobs? What is the human and societal impact? 4.) How does Brandon think about vulnerability in leadership? Why does Daniel and Brandon's relationship work so well today? What has Daniel (Founder) taught Brandon about communicating that vulnerability the right way and authentically? What does Brandon advise founders in terms of being open to their vulnerabilities? 5.) What are the biggest challenges in scaling an organisation to the 1,000+ person organisation that UiPath is today? What breaks When does it break? How does one maintain culture wit such scale? What have been the challenges of building a truly global business from Day 1? How do they look to mitigate them? Items Mentioned In Today's Show: Brandon's Fave Book: The Five Temptations of a CEO: A Leadership Fable As always you can follow Harry, The Twenty Minute VC and Brandon on Twitter here!

20 Joulu 201937min