20VC: Why People Should Never Be Surprised If Fired, Subscription E-Commerce Is Hot & People Never Give True and Direct Feedback with Amir Elaguizy, Co-Founder @ Cratejoy

Todd McKinnon is the Co-Founder & CEO @ Okta, the identity layer for the internet, providing one trusted platform to secure every identity, from customers to your workforce. Prior to their IPO in 2017, Todd raised over $229M for the company from some of the best in the business including Sequoia, a16z, Greylock, Khosla and Floodgate to name a few. Prior to founding Okta, Todd was VP of Development @ Salesforce.com where he spent an incredible 5 years and before that enjoyed an 8 year run in the software development team @ PeopleSoft. In Today's Episode You Will Learn: 1.) How Todd made his way into the world of startups with PeopleSoft and Salesforce? What was the a-ha moment for Todd with the founding of Okta? What were the biggest management takeaways from his time with PeopleSoft and Okta? How did Todd convince his wife that leaving a safe job with Salesforce to found a company was the right decision? 2.) How does Todd approach decision-making today? What frameworks does he use to optimise his decisions? How does Todd analyse reversible vs irreversible decisions? How does Todd know when he has done enough work and is ready to make the decision? Who does he debate the most important decisions with? 3.) What does Todd believe makes for a truly great enterprise software entrepreneur today? What were the first elements to break in the scaling of Okta? When is the right time to hire your first recruiters and Head of People? What should you look for in those people? How did Todd make mistakes when it comes to hiring recruiters? 4.) What are Todd's biggest lessons on successful board management? How would Todd describe his style of board management? How has it changed over the years? What can CEOs do to extract the most value from their board? What were the biggest mistakes Todd made in the early interactions with his board? 5.) How does Todd balance the growth expectations of Wall St on a quarter by quarter basis with the long term vision and strategy? Why does Todd believe that Okta has been able to make the transition from unsexy to one of Wall St's most loved companies? What is the secret to investor relations as a public company? Item's Mentioned In Today's Episode Todd's Favourite Book: Slaughterhouse 5 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.

22 Feb 202141min

Assaf Wand is the Founder & CEO @ Hippo Insurance, with over $700M in funding Hippo are setting a new standard for home insurance and offer protection for what's important to today's homeowner. Nima Ghamsari is the Founder & CEO @ Blend, with over $665M in funding they are the digital platform streamlining the journey from application to close — for every banking product. Max Simkoff is the Founder & CEO at States Title, with $229M in funding States Title are using machine intelligence to create a vastly more simple and efficient closing experience for lenders, real estate professionals, and homebuyers. Brendan Wallace is a Co-Founder and Managing Partner at Fifth Wall, with over $1.3Bn in commitments and AUM across multiple different vehicles, they are the largest venture firm focused on the real estate industry and property technology for the Built World. In Today's Episode You Will Learn: 1.) 3 of the largest and most successful founders in the financial real estate market, what have been their biggest learnings from their friendship over the last 5 years? What have been some of the most hotly debated topics they have had as a group? How did their opinions and views change as a result? 2.) How do they think and feel about the tech exodus from Silicon Valley, temporary movement due to COVID or fundamental shift? How closely correlated is the move out of California with the explosion of liquidity from IPOs and acquisitions? What pisses Max off most about people leaving CA currently? 3.) How have their roles as leaders changed in the time of COVID? What have been the most challenging elements? What have they had to embrace? What have they had to disregard or stop? What advice do they give to other founders scaling into hyper-growth in a remote format? 4.) What do they believe is the fundraising strategy that allowed them to raise over $1.5Bn as a group? How do they think about what they look for in each stage of investors? How does it change when entering growth stages? How has their experience been having corporates play a large role in their financing? What are the biggest challenges of working with corporates? What does one need to do to extract the most value from them? Item's Mentioned In Today's Episode Max's Favourite Book: A Heartbreaking Work of Staggering Genius 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.

18 Feb 202144min

Christian Reber is the Founder & CEO of Pitch, the collaborative presentation software for modern teams. To date, Christian has raised over $52M for Pitch from some of the best in the business including Index, Thrive, Blueyard and then some amazing individuals including Instagram's Kevin Systrom and Mike Krieger, Zoom's Eric Yuan, Datadog's Olivier Pomerol and Tiny's Andrew Wilkinson. Prior to Pitch, Christian was the Founder @ Wunderlist, raising $35M from the likes of Sequoia and Atomico before being acquired by Microsoft. In Today's Episode You Will Learn: 1.) How Christian Reber made his way into the world of startups? How that led to his founding te global phenomenon, Wunderlist? How his experience with Wunderlist led him to start Pitch most recently? 2.) Does Christian regret selling Wunderlist to Microsoft? What was the reasoning and logic behind it? What does Christian believe Microsoft did wrong that resulted in Wunderlist no longer being in existence today? How did Christian deal with the personal depression post the sale of Wunderlist? 3.) How does Christian assess and evaluate his personal relationship to risk? What does he do when making risky and large decisions to ensure he is comfortable? How does Christian feel about his relationship to money? How has it changed over time? How does Christian approach personal finance today between startup investing, fund investing, cash and savings? 4.) How does Christian think about what great product design means today? How does he balance gut and instinct with granular data when making product decisions today? How has this changed over time? How has Christian structured his team to make the fastest and most efficient product decisions? 5.) How would Christian reflect on his own style of board management? How has it changed over time? What element does he still to this day find most challenging? What board moment would he say is his most memorable? Who has been his favourite board member to work alongside? Item's Mentioned In Today's Episode Christian's Favourite Book: The Unbanking Of America: How the New Middle Class Survives 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.

15 Feb 202136min

Matan Bar is the Co-Founder & CEO @ Melio, the company that provides the simplest way to pay vendors and contractors. To date, Matan has raised over $254M for Melio from the likes of Accel, Bessemer, Aleph, Coatue and General Catalyst to name a few. Prior to founding Melio, Matan Bar was Head of PayPal Consumer Product Center and before that was a Head of Product and GM @ eBay in their Israel Innovation Center. In Today's Episode You Will Learn: 1.) How Matan Bar made his way into the world of startups and came to found one of the fastest-growing companies today in the form of Melio? 2.) What is the single most important thing in a financial transaction business? How does Matan think about the balance between optimising for transaction volume vs revenue? What does Matan believe are the core network effects within payments businesses? Why do most opt for closed network effects? How is Melio different? 3.) What have been some of the biggest challenges of adding 170 people in one year? What breaks first? What needs to be in place to ensure the culture can scale with the headcount? How does Matan structure the leadership team to manage this hyper-growth? Has Matan struggled with self-doubt in his leadership during this hyper-growth? 4.) What specifically has Melio and Matan done to achieve a 49% female to male ratio within the company? What works when it comes to implementing diversity at scale? Where do so many people make mistakes? What specific strateies have allowed Melio to hire some of the best female engineers? 5.) How does Matan most like to interact with his board? How does he determine the advice to ingest vs the advice to reject? What have been some of his biggest lessons when it comes to successful board management? Where do many first time founders make mistakes when it comes to investor value add and extraction? Item's Mentioned In Today's Episode Matan's Favourite Book: The Unbanking Of America: How the New Middle Class Survives 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.

11 Feb 202134min

Michael Eisenberg is a Co-Founder and Equal Partner @ Aleph, with over $550M under management and a portfolio including the likes of Lemonade, Melio and HoneyBook, they are one of the leading early-stage firms of the last decade. Prior to founding Aleph, Michael spent 15 years as a General Partner @ Benchmark and before that, made his way into venture with Israel Seed Partners where he built an incredible portfolio over an 8 year period. If all of this was not enough, Michael is also an author having published 4 books. In Today's Episode You Will Learn: 1.) How Michael made his way into venture over 25 years ago and how his 15 years at Benchmark led to his founding Aleph? 2.) How has seeing multiple booms and busts impacted Michael's investing mindset? What do many misunderstand when it comes to reserve allocations in market cycles? Why does Michael believe busts are more psychologically impactful than financially impactful? 3.) How does Michael approach portfolio construction with Aleph today? How does Michael think about the right level of portfolio diversification? How does Michael think about the right level of capital concentrated into one company? How does Michael assess the difference between risk and uncertainty? What do many misunderstand between the two? 4.) Why does Michael believe in generalist VCs over specialist VCs? Why do they win? Why does Michael believe in small boutique firms vs large multi-stage firms? How does Michael think about the notion of ownership on first check? Is it possible to really build ownership across rounds today? 5.) How does Michael reflect on his own style of board membership today? How has it changed? What have been some of Michael's biggest lessons on board membership from Bruce Dunlevie @ Benchmark? What advice does Michael have to newer investors joining boards for the first time? Item's Mentioned In Today's Episode Michael's Most Recent Investment: Melio 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.

8 Feb 202144min

Justin Fishner-Wolfson is founder and the managing partner of 137 Ventures, a growth-stage venture firm that provides customized liquidity solutions to founders, investors, and early employees of high-growth private technology companies. Their portfolio includes the likes of SpaceX, Wish, Anduril, Flexport, and Rigup to name a few. Previously, Justin worked on the investment team at Founders Fund and before that served in the US Department of State under Alan Larson, Undersecretary for Economic, Business and Agricultural Affairs. In Today's Episode You Will Learn: 1.) How Justin made his way into the world of venture with Founders Fund and how that led to his founding 137 Ventures? What specific lessons did he learn from Peter Thiel that he has applied to his investing mindset? 2.) What does Justin mean when he says, "it is the last double that matters"? Why does Justin believe that liquidity aligns incentives between VCs and founders? When is the right timing for this liquidity and are there limits to the sizes of secondaries founders and teams should take? 3.) How does Justin think about his own price sensitivity today? Why does Justin believe that the conventional VC views on ownership are outdated and no longer as relevant to this class of company? How does Justin think about diversification among the portfolio today? What is the right level? What is too diversified? What is too concentrated? 4.) Why does Justin believe that standard thoughts around CAC/LTV are wrong? How have they changed over time? How should founders think about this and present these metrics to investors? Given these metrics, how does Justin feel about the revenue multiples we are seeing today both in private and public markets? Item's Mentioned In Today's Episode Justin's Favourite Book: The Hitchhiker's Guide to the Galaxy Justin's Most Recent Investment: Lattice 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.

4 Feb 202139min

Ilkka Paananen is the Co-Founder & CEO @ Supercell, the makers of some of the most wildly successful games of the last decade including Hay Day, Clash of Clans, Boom Beach and more. Prior to Tencent acquiring a majority stake in the company at a reported $10.2Bn acquisition, Ilkka raised over $143M for the company from Accel, Index, Atomico, IVP, LVP, Initial and Lifeline. Throughout his incredible leadership of Supercell he has coined the term, "the least powerful CEO", a fascinating concept and one we dig into in this episode. In Today's Episode You Will Learn: 1.) How Ilkka made his way into the world of startups and came to found one of Europe's most valuable companies in the form of Supercell? 2.) How does Ilkka think about his own relationship to risk? Why does Ilkka believe the No 1 reason companies die is due to their relationship to risk? How does Ilkka evaluate his relationship to money? How has it changed? How does Ilkka feel the weight of responsibility with his wealth? 3.) What does being "the least powerful CEO" mean in practice? What does Ilkka belive is key for leaders to really empower their team to be bold and ambitious? How can leaders create environments of safety where it is ok to fail? Where do many leaders go wrong here? 4.) The first 3 Supercell games were failures, how did Ilkka deal with those really hard times? How can leaders sustain morale in such hard times? Supercell then had 3 big hits in a row, how does one prevent ego and over-confidence in teams? What is the beer vs champagne culture? 5.) How does Ilkka think about the importance of focus? What has Ilkka done and learned to be a much more focused leader? How does Ilkka approach the aspect of competition today? Item's Mentioned In Today's Episode Ilkka's Favourite Book: What You Do Is Who You Are: How to Create Your Business Culture by Ben Horowitz 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.

1 Feb 202129min

Hubert Palan is the Founder & CEO @ ProductBoard, helping product managers understand what customers need, prioritize what to build next, and rally everyone around the roadmap. To date, Hubert has raised over $64m for ProductBoard from the likes of Sequoia, Index, Kleiner Perkins, Bessemer and Credo Ventures to name a few. Prior to founding the company, Hubert was VP Product Management @ GoodData where he played an instrumental role in their scaling from 6 to 300 people. In Today's Episode You Will Learn: 1.) How Hubert made his way from Eastern Europe to SF, made his way into the world of product management and came to found ProductBoard? 2.) Why does Hubert believe that "founder insight" is overrated? What strategies and tactics does Hubert give to founders to be more mentally plastic and flexible? How does one know when to persist when things are not working vs when to give up? What is the decision-making framework? 3.) Why does Hubert believe that "big and bold product vision can be dangerous"? How does Hubert think about when is the right time to release a second product? What are the core elements to tackle when thinking about a second product? Where do many make mistakes here? 4.) Why does Hubert believe that, "if you get to product market fit by accident, you could be in trouble?" What does Hubert advise in terms of studying if and how you got to product market fit? How can one use post-mortem analyses here effectively? 5.) Why does Hubert believe that transparency is so necessary today with the team? Should founders be transparent when it comes to M&A, fundraising etc? Where are the limits? What makes it so hard to instil effectively? What do many founders misunderstand? Item's Mentioned In Today's Episode Hubert's Favourite Book: Elad Gil's High Growth Handbook 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.

29 Jan 202139min