Sebastian Siemiatkowski is the Founder and CEO @ Klarna, the company that makes online shopping simple, allowing you to buy what you need today and pay later. To date, Sebastian has raised over $2.1Bn for the company from the likes of Sequoia, Silver Lake, Blackrock, DST, Northzone, Creandum and even Snoop Dog to name a few. Klarna has been an incredible 16-year journey for Sebastian with it now being the most valuable private technology company in Europe with over 3,500 employees.
“People talk about it like there's this learning curve, and the best spot is at the place where you're challenged to the precise point where you're almost giving up, but not entirely. That's exactly it.
“And I have this amazing swim teacher for my children, her name is Petra, and she's just fantastic. I just love watching her because she has this ability of taking my children in the pool and pushing them to that exact point where they are almost, almost giving up, and they're learning at such a pace. And if I can recreate such an environment in Klarna, if I can create an environment, if I can be part of creating an environment where we put people in that position where they just are exactly at that curve where they are challenged, supported, and kind of at the edge and being given the ability to learn really fast and really discover what it means to have an impact.”
“I don't think that much about what other people or other companies or other things out there could have done different. And there's pros and cons to that. But the benefits of that is that it speeds up my learning. Because a lot of people – and I've realized that as I manage other people – is that because they're so obsessed with trying to think about what other people could have done differently, and why situations arose, and why it wasn't their responsibility and so forth, they spend a lot of time on that, because we've unfortunately been brought up in some kind of guilt that it's bad to do wrong, and it's bad if it's our fault, and you want to avoid that.
“And these psychological constraints, unfortunately, hinder people from developing much faster, because if you go into every situation and say, the only thing that's relevant here is what I could have done differently, what I could have learned from this – if that's the only thing, it's just like, whatever, I accept my responsibilities. What could I have done differently? If you only focus on that, you just learn much faster.”
“I think self-doubt is not nothing. It's not a bad thing, right? It's a very healthy thing, if it represents you continuously trying to understand, am I doing the right thing? Is this something that I want to do? Am I making the right decisions? So I think it's extremely healthy to do that. I'm not saying it's not painful or tough when you have it. But I think it's a very positive thing.
“I'm much more worried when people tell me they have no self-doubt. And then I'm like, uh-oh, because that means that you're not really reflecting on your actions, and you're not learning from them. So I wish I could give you something more comforting than that, but I would actually say enjoy it. Be happy that you have it, and it's gonna make you a better person.”
“I love the fact that Michael Moritz wrote this book that I still haven't read, so it's kind of funny that I'm referring to it, but he wrote this book about Ferguson, that manager of Manchester United. And I think it's very relevant, because today, the saying is that for people to be motivated at work, they need to have a higher purpose, the company needs to do something good, and so forth. And I am not disputing that, that is very true that it contributes to people's sense of purpose, and so forth.
But before you even get to that level, we have to ask ourselves, what is it really that makes people motivated and enjoy themselves? And I think when I think about that, I often look at sports, because why do people love soccer? What's the higher purpose of winning Champions League? People say, oh, there's a massive higher purpose, but not entirely, you're not really making the planet better by winning. Still, people are massively engaged in these things. Why?
“Because it's a team effort, there are clear roles, you know exactly what you're supposed to do – I'm supposed to put the ball in that score. And then it's very clear how you win, there is a referee that stops people from cheating. And so there's a lot of things in that environment that makes it motivating, that makes people engaged, and those things are usually lacking in companies.”
“The problem with a company is that it's a much more complex environment with a lot of other things going on in parallel in people's lives. And so I have definitely occasionally missed to see that people are beyond that point.”
“In Sweden, there's this course called Situation Adopted Management, which basically means that there is no single management technique. You look into the situation, you try to understand it from multiple angles. And then depending on where that individual is, and how you perceive the mental status, and the mood of that individual, and so forth, you try to adapt. Either you coach or you challenge or you instruct or you do different things. There's not a single methodology that will allow you to deal with those situations. But a lot of it is empathy. It's the ability to look at people and read them, and try to understand, and ask them questions, and understand where they are.”
“I think a lot of times as a company grows, what ends up happening is the thing just becomes so complex. So management tries to organize the company in a way that makes sense to them and that is easy to understand for them. But the consequence of that often, unfortunately, is it makes no sense for the person who's actually doing the job. So they lose the purpose. Why am I coming to work? What are we trying to achieve? All of these things get lost.
“So what we said is, we have to do the exact opposite. The critical element is that the people who are actually supposed to do something – not the manager – the people actually supposed to do something, if they program or to do a marketing campaign, or whatever they're doing, they need to come to work every day and feel I know exactly why I'm coming, I know how I'm contributing, I know who I'm contributing for, I know what value I'm creating.
“And if that thing creates tons of complexity for us, as managers, because the whole system becomes much more complex, then that's what we're getting paid for. That's the one. That's why we're getting a good salary. Because we need to manage that complexity.”
“Keep very close on the recruitment … Especially in a country like Sweden, a country where a typical saying is, alla ska komma med, which means, everyone should come, everyone should join. And it's very nice. And I appreciate that with Swedish culture, I'm not trying to really call it. I think it's fantastic and it's a fantastic society. But as a consequence, it took us some time to conclude something which maybe in the US or maybe even in the UK as it would have been much more obvious, which is that it's not a company for everyone. It is a company for the people that want to have that challenge, that want to be in that environment, that think that's interesting, that want to learn a lot fast, and want to get a lot of things done. And that's not everyone, and that's okay.
“Like when you play soccer – some people play soccer for fun, other people play to win the Champions League. People do it for different reasons. And they have different ambitions with it and different objectives with it. And the same applies to us.
“So it took us some time to realize that we need to tell people, look, just so you know, this is not going to be your standard company, you're going to be expected to do a hell of a lot of things, you're going to be expected to be challenged, you're going to expect it to do your utmost. And we're going to try to support you and help you and grow. So just know what you're getting into, before you get into it.”
“One thing I would say, it's going to be a much smaller industry. And that's because it is ridiculous that moving money back and forth is a trillion-dollar industry. That is ridiculous. There is no good reason for that whatsoever. This is going to be a much more cost-efficient, much smaller revenue business than it is today. But even though it would be much smaller than it is today, it's still massive, and Klarna has the opportunity to be one big player in that industry, similar to what Tesla is doing in cars or whatever, that's what I want to do. And I feel we have all the prerequisites to accomplish that.”
“There's going to be this push that's going to transform this industry and the people are going to lose on it are the suits in the marble offices in the city centers. That's where the pain is going to be felt, but the winner is going to be the consumer.”
“It's a little bit like self-driving cars – we all know it's going to happen, the question is when. And based on what I've seen in the last 15 years, and I've seen how retail has gone from retail to ecommerce and all these trends, this decade is going to be the disruption of retail banking.
“At the end of this decade, there will be a couple of new total players that will be very dominating in this space, and the rest will either cease to exist, will merge and try to acquire some of the new ones, or maybe a few of them will manage to reinvent themselves. But this is going to be an extremely interesting time.”
Sebastian’s Favourite Book: The Neverending Story
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Patrick Spence is the CEO @ Sonos, the sound experience company connecting millions of listeners around the world to the content they want. Prior to their IPO, they raised over $450M from the likes of Mike Volpi @ Index, Satish @ Redpoint and e.ventures to name a few. As for Patrick, prior to Sonos, he spent an incredible 14 years with RIM (makers of Blackberry) across multiple different roles.
In Today’s Episode You Will Learn:
1.) How Patrick made his way into the world of tech and startups and became an instrumental part of the exec team at Blackberry? How that led to his joining Sonos as COO and later becoming CEO?
2.) How did building and growing RIM influence everything that Patrick does at Sonos? From the battle with Apple, what were Patrick's biggest lessons on the right way to approach competition? How does Patrick think about both partnering with Google today whilst also suing them at the same time?
3.) From COO to CEO: How did Patrick make the transition from COO to CEO so successfully? What were the most challenging elements to scale into? How does Patrick empower his team to have the confidence to stand up and say no to the CEO? How can one encourage debate and dissent in the team?
4.) How does Patrick feel about the role that vulnerability has to play in leadership? How does Patrick approach his own self-doubt as a leader today? How does he manage it? How does he advise founders unsure if they can scale into their leadership roles? What mentors does Patrick have? What has he learned from them?
Item’s Mentioned In Today’s Episode
Patrick’s Favourite Book: The Infinite Game: How Great Businesses Achieve Long-Lasting
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Jeremy Liew is a Partner @ Lightspeed Venture Partners, one of the leading firms of the last decade with a portfolio including the likes of Affirm, Snapchat (Snap), Mulesoft, Epic Games, Carta and more amazing companies. As for Jeremy, in the past he has led deals and sat on the boards of Snap, Affirm, Blockchain.com and The Honest Company to name a few. Before Lightspeed, Jeremy was with AOL, first as SVP of corporate development and chief of staff to the CEO, and then as general manager of Netscape. Due to his incredible investing success, Jeremy has been featured on the Forbes Midas List multiple times.
How Jeremy Liew first heard about Evan Spiegel and Snapchat?
"It's actually kind of a roundabout story. We first heard about Snapchat, because one of my partners Barry Eggers is a very involved dad. And he noticed that his daughter had started taking weird selfies"
What was the process to first get in touch with Evan?
"The challenge was, the website only had info at Snapchat email address was the only info The only contact info available. So I emailed them, and I never heard back.
Why was it such a challenge?
"I then looked up Snapchat on LinkedIn, and I couldn't find any contact information. And I was in a little bit of a loss, I wasn't getting any responses from the email, there was nothing listed on LinkedIn. So I ended up doing a who is look-up to try to find out who had registered the Snapchat URL, and I got an info@ snapgrouplimited email. So I emailed that. And then as again, I didn't get any response.
What was the breakthrough in the end?
"....Finally, what I decided to do was since Evan was a student at Stanford, and since I graduated from Stanford for business school, at that time, Facebook allowed you to message people who were in the same network, and Stanford constituted that. So I messaged him through Facebook, and I finally got a response. But this time, I got a response within five minutes."
What are the 4 things Jeremy looks for when making an investment in consumer?
Why does Jeremy believe that usage with young females is the biggest predictor of future consumer social success?
"Generalising, Women build their relationships through, you know, conversations, and they build those relationships through sharing information with each other. And obviously, that sort of conversation or relationship is a fantastic conduit for word of mouth for anything that people really appreciate."
In what ways does Jeremy like to see consumer social companies become part of pop culture?
"Today, if you think about whether it be social networking, apps, messaging, e commerce, streaming media, it's all part of pop culture. And so as much as movies or television or music or dance, and so if you ask yourself who are the early adopters of pop culture"
What are examples of this?
"Social networking, apps, messaging, e commerce, streaming media, it's all part of pop culture."
Did the market evolve the way that Jeremy thought it would?
"And one of the things that surprised us a little bit was that this was very strong in Southern California, Northern California, and Georgia, when we first invested and parts of the South"
What was a surprise to Jeremy Liew in terms of market evolution?
"In Norway, which had actually transcended, that sort of high school and college-age population, in fact, become the number three most downloaded app, most popular app, in Norway at that time. So ahead of Instagram, ahead of Facebook, and so forth. And so that's what I think gave us that early indication that the app was going to be able to break out beyond its high school, college student, initial starting point, not just in the US, but everywhere"
What did the Snap user to install count look like at the time?
"In, you know, March, April of 2012, they had about 90,000, daily active users off of the base of 180,000 installs."
How does this compare with many others in the consumer social space?
"That's a very, very high ratio."
What were Snap's retention numbers at the time?
"50% retention after 90 days, which again, suggests high engagement, high retention, high growth that speaks to upside volatility"
How did Snap's frequency of usage on an individual basis look like at the time?
"So people were opening the app six times per day, they were opening at least once every second day."
Across, retention, usage and user to install, what are the benchmarks for great, good and average?
" I would say as a rule of thumb, in messaging and social networks, you would want to see at least a DAU to MAU ratio of north of 50%. And you would want to see at least a D 30 of say 30 to 40%, for your for something to really be working to be sort of at that outlier level."
What unique insight does Jeremy believe that Evan always held for the company and the product?
"One of the things that was so special about Evan, and that I think, has continued to contribute to the success of the company has been that he's always been able to do that to look at something with fresh eyes, and not iterate over what the current state of the art is that, you know, just from first principles basis"
How has Jeremy seen Evan change and evolve as a leader?
"I think his maturity as a business leader, as a leader of people, as a manager, you know, as a strategist, although he always had very good strategic instincts, but they've just continued to grow and evolve and blossom."
What were some of the big inflection points in his development?
"So you know, the feed has always been up until this point, in reverse chronological order, I think largely because that's what friendster do choose to do. And then Evan comes along. He says, How do you tell stories beginning, middle, end. Now go to social media? How do they tell stories in reverse chronological order means and middle beginning? Well, that doesn't make any sense. And so he said, we're going to create a whole new feed of stories, and they're going to be told in chronological order beginning middle end."
Who are some unsung heroes from the Snap journey that were transformational?
"Bobby doesn't get enough credit. From the very beginning from I think maybe a couple of months in was thinking about the breakthroughs that had been happening computer vision and the implications for what that could build....Imran Khan, he really helps take a lot of the load off of Evan allowed me to focus on product engineering, he took over sales and monetization Ops, he did a lot of the financing work in the time when Snapchat raised a lot of capital."
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.
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
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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
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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
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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
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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
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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
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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
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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
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Alfred Lin is a Partner @ Sequoia Capital, one of the world's most renowned and successful venture firms with a portfolio including the likes of Google, Airbnb, Whatsapp, Stripe, Zoom, Doordash and many more. As for Alfred, he has led deals in the likes of Airbnb, Doordash, Instacart, Reddit and Houzz to name a few. Prior to the world of venture, Alfred was Chairman and COO @ Zappos for 6 years leading to their acquisition by Amazon.
In Today’s Episode You Will Learn:
1.) How Alfred made his way into the world of venture and came to be a Partner @ Sequoia? How Alfred first met DoorDash? Where did the meeting take place? Who was there? What were the first impressions?
2.) Market: How did Alfred breakdown the food delivery market when doing the diligence for the investment? How did Alfred forsee the market changing over time? What were some unexpected elements of the market Alfred did not forsee? What does Alfred look for in markets; size or growth?
3.) Competition: How did Alfred analyse the competitive landscape for food delivery at the time? Why does Alfred believe that great companies are not built by focusing on the competition? What does Alfred mean when he says, "you have to be customer-obsessed and competitor aware"?
4.) Traction: Does Alfred agree with Sarah Tavel in the dangers of chasing topline GMV? What negative behaviours can chasing GMV trigger? What does Alfred mean when he says, "founders have to be able to distinguish between input and output metrics"?
5.) Acquisition: What does Alfred believe DoorDash did so well in terms of acquiring drivers more efficiently? How did they retain them so effectively? What allowed DoorDash to compete so effectively when it came to merchant acquisition? What were some of Alfred's biggest takeaways when it came to DoorDash's customer acquisition journey?
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Phil Libin is the Founder and CEO @ mmhmm, the app that allows you to level up your remote presentations, making high-quality video content in minutes. To date, Phil has raised over $30M for the company from an incredible investor base including Sequoia, Kevin & Julia Hartz, Tony Fadell, Instagram's Kevin Systrom and Mike Krieger and Brianne Kimmel. Prior to mmhmm, Phil was a Managing Director @ General Catalyst and prior to his time in venture, Phil most famously founded Evernote, where he led the business with phenomenal success, as CEO for over 8 years.
In Today’s Episode You Will Learn:
1.) How Phil made his way into the world of startups, came to found Evernote and how that led to his founding of mmhmm, most recently?
2.) How would Phil describe his management style today? How has it changed over time? Why does Phil believe shortcuts are the greatest mistakes startups make? What does Phil believe you can vs cannot take shortcuts on? What have been some real world lessons there?
3.) What were Phil's biggest takeaways from his time in venture? How did it change his operating mindset? Does Phil believe there is an incentive misalignment between founder and VC? Why is Roelof Botha the best board member Phil has worked with? What makes him so special?
4.) How does Phil think about the unbundling/verticalisation of Zoom? How does he predict the market evolving? How does Phil see the differing usage patterns between consumer and business? Why does Phil believe more can be learned from looking at similarities and not differences?
5.) What does Phil believe are the two classes of mistakes when scaling startups? What have been Phil's biggest lessons on acquiring and retaining the best talent? How does Phil create an environment of dissent where anyone can bring their entire self and beliefs to the table?
Item’s Mentioned In Today’s Episode
Phil’s Favourite Book: Kafka on the Shore
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Andrew Dudum is the Founder & CEO @ Hims & Hers, offering a modern approach to health and wellness and one of the fastest-growing companies to reach $1Bn. Prior to their going public on Tuesday this week, Hims raised over $158M from some of the best including Thrive, Forerunner, Founders Fund, IVP, Redpoint and more. As for Andrew, alongside his role at Hims he is also Co-Founder of Atomic, a company builder and venture fund all in one, backed by Peter Thiel and Marc Andreesen to name two. Prior to Atomic, Andrew led product at TokBox managing a team of 30 leading to their acquisition by Telefonica in 2012.
In Today’s Episode You Will Learn:
1.) How Andrew made his way from Head of Product at Tokbox to venture capitalist with Atomic to changing healthcare with Hims?
2.) What are the biggest misconceptions people have with regards to what it takes to build a successful company? Why do you not need big teams? How can leaders drive efficiency within small teams? What have been Andrew's biggest lessons in acquiring the best talent in market? What works?
3.) Hims is the fastest company to scale to $1Bn, how does Andrew reflect on how he managed hyper-growth? What did he do well? What was the first to break? What would he do differently? When is the right time to go from generalist to specialist? When is the right time to add more products?
4.) Why did Andrew believe now was the right time to IPO just 4 years into the founding of the business? How did the SPAC process play out? What are the core advantages to Andrew of the SPAC over an IPO? Why will more founders use it in the future? How does Andrew assess the importance or lack of, when it comes to the pricing pop on IPO day?
5.) How does Andrew reflect on his relationship to money? Why does he feel more scared of it now than ever before? How does he think about bringing up his children with an appreciation and respect for money? What 3 traits would Andrew most like his children to have?
Item’s Mentioned In Today’s Episode
Andrew’s Favourite Book: The Planet Remade: How Geoengineering Could Change the World
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Josh Silverman is the CEO @ Etsy, leading the company as it builds a platform that empowers creative entrepreneurs around the world. Prior to their IPO, Etsy raised funding from some of the best in the business including Danny Rimer @ Index, Albert Wenger @ USV and Jim Breyer @ Accel to name a few. Prior to Etsy, Josh served as President of Consumer Products and Services at American Express, was the CEO of Skype, and CEO of shopping.com, and he held various executive roles at eBay. Josh is also currently on the board of directors of Shake Shack.
In Today’s Episode You Will Learn:
1.) How Josh made his entry into the world of startups, came to be CEO of Skype and how he came to be CEO of Etsy? How did Josh's political background prepare him for being a public markets CEO?
2.) How does Josh think about 10 year plans? What is the right alternative? What does Josh do when he does not know what to do? How does Josh think about head vs heart in decision-making? How does Josh think about downside protection and risk mitigation with decisions?
3.) Why does Josh believe that you should, "never let a crisis go to waste"? How does he interpret that? Does Josh believe you learn more from success than failure? Why does Josh believe many succeed in spite of, not because of? How does Josh connote happiness to a milestone of success? What is true happiness for Josh?
4.) How does Josh think about winning today? What is the framework Josh believes founders need to put in place to optimise their chance of winning? How does Josh structure his team at Etsy to optimise for speed and experimentation? What has worked? What has not worked?
5.) How can leaders create a system where failure is minimised? How does Josh implement a "red hat vs green hat" decision making process around new ideas at Etsy? What question does Josh and the team ask with every experiment? How should one analyse the cost of rolling back a decision?
6.) How does Josh determine between dogma and good practice in a company? What is the right way to remove antiquated dogma without damaging morale? What were some of the biggest challenges from his doing this on entry at Etsy?
Item’s Mentioned In Today’s Episode
Josh’s Favourite Book: Grant
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Ali Ghodsi is the Founder & CEO @ Databricks, bringing together data engineering, science and analytics on an open, unified platform so data teams can collaborate and innovate faster. To date, Ali has raised over $897M for the company including from the likes of a16z, NEA, Microsoft, Battery, Coatue, Greenbay and more. Prior to Databricks, Ali was one of the original creators of open source project, Apache Spark, and ideas from his research have been applied to Apache Mesos and Apache Hadoop.
In Today’s Episode You Will Learn:
1.) How Ali made his way from fleeing Iran as a refugee to living in a Swedish ghetto? What was the founding moment for Ali with Databricks?
2.) How does Ali think about and evaluate risk today? Why does Ali always make his team do downside scenario planning? How does Ali think about his relationship to money today? Why does Ali disagree with gut decisions? What is his process for making decisions effectively?
3.) Stage 1: The Search for PMF: What are the core elements included in this phase? What types of leaders thrive in this phase? What type struggle? How can leaders sustain morale in the early days when it is not up and to the right? Who are the crucial hires in this phase?
4.) Stage 2: Scale Go-To-Market: What are the core roles needed to expand GTM fast and effectively? Why should you hire sales leaders before marketing leaders? Why is hiring finance leaders so crucial here? What mistakes are most often made here? How do the board resolve them?
5.) Stage 3: Process and Efficiency: What are the first and most important processes that need to be implemented? How does Ali need to change the type of leader he is to fit this stage? How does one retain creativity and nimble decision-making at scale and with process?
Item’s Mentioned In Today’s Episode
Ali’s Favourite Book: Good Strategy Bad Strategy: The Difference and Why it Matters
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Annie Duke is a former professional poker player and the author of National Bestseller, "Thinking in Bets" & "How To Decide". During her poker playing days, Annie was a World Series of Poker bracelet winner, the winner of the 2004 Tournament of Champions and the only woman to win the NBC National Poker Heads Up Championship. Today, Annie is also the founder of How I Decide, a non-profit that creates curricula and tools to improve decision making and critical thinking skills for under-served middle schoolers.
In Today’s Episode You Will Learn:
1.) How Annie made her way from professional poker player to National Bestselling author and coach to the world's leading investors?
2.) How does Annie evaluate the nature of risk? What is good risk vs bad risk? How does Annie think through reversible vs irreversible decisions? What is her framework? Why does Annie believe most irreversible decisions are actually reversible? How does it change your thinking?
3.) How does effective solo-decision-making differ from effective group decision-making? What decision-making biases does Annie often see venture being guilty of making? What 3 things can one do to improve the decision-making of the collective group?
4.) How does Annie think about sunk cost? How does one know when enough is enough and you have to walk away? How does this tie into Annie's thinking on portfolio theory? How does Annie think about pre-mortems? How should they be structured? What is included?
5.) How does Annie define critical thinking? What tips would Annie give to someone in really advancing their level of critical thinking? What behaviours can one implement to seek to protect critical thinking? How does this differ in team environments?
Item’s Mentioned In Today’s Episode
Annie’s Favourite Book: The Success Equation: Untangling Skill and Luck in Business, Sports, and Investing
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Biz Stone is best known as the Co-Founder of Twitter and Medium. Biz is also an investor in the likes of Slack, Square, Intercom, Beyond Meat and Blue Bottle Coffee. Biz also co-founded Jelly, a "human in the loop" AI search service, which was acquired by Pinterest. Due to his many successes, Biz has been recognized as INC Magazine Entrepreneur of the Decade and one of TIME's 100 Most Influential People in the World.
In Today’s Episode You Will Learn:
1.) How did Biz make his way into the world of startups and come to found Odeo/Twitter one day on a car trip with Ev Williams?
2.) How does Biz evaluate his relationship to money? How does Biz think about teaching his son the value of money? What does Biz mean when he says wealth 'accentuates your current self"? How did Biz get off the treadmill of always wanting and chasing more?
3.) How does Biz think about insecurity and self-doubt? How does Biz approach saying no? How does he get comfortable with not always being Mr Popular? What is so challenging here? How does Biz feel about founding tieing their identities to their company?
4.) Why did Biz come back to Twitter in 2017? With hindsight, what would he have done differently if he were to return again? What were the biggest challenges when he arrived? Why was internal morale low? What did he and Jack do to increase it? What worked? What did not?
5.) Why does Biz not feel Silicon Valley is an "insider-only" universe? Why does Biz feel Silicon Valley is a mindset? How does Biz think about the decentralisation of talent moving forward? How does Biz compare the UK to the US startup ecosystem? What is worse in the UK?
Item’s Mentioned In Today’s Episode
Biz's Favourite Book: Emergence: The Connected Lives of Ants, Brains, Cities and Software
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Howard Marks is co-chairman and co-founder of Oaktree Capital Management, a leading investment firm with more than $120 billion in assets. Prior to founding Oaktree, Howard spent 10 years at The TCW Group, where he was responsible for investments in distressed debt, high yield bonds, and convertible securities. Howard has also written two books, most recently Mastering the Market Cycle: Getting the Odds on Your Side, and it was Warren Buffet who said, “When I see memos from Howard Marks in my mail, they’re the first thing I open and read. I always learn something.”
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.
In Today’s Episode You Will Learn:
1.) In March Ray Dalio stated we would be entering a "global recession", how do Howard and Bill feel about this statement? How does today's environment remind Howard and Bill of 2010/11? What is similar? What is different? How does Bill think about investing through cycles?
2.) How does Bill think about investing through cycles? What have Bill's lessons been from seeing many venture vintages on LP performance across cycles? How does Howard think about investing through cycles from a distressed debt perspective? What have his lessons been from Oaktree's performance over the years?
3.) Do Howard and Bill agree we will not see interest rates go anywhere for the next 3-5 years? What is the impact of this sustained low-interest rate environment? What could be done that would see interest rates increase in the future? How does Bill believe this will impact the supply of LP dollars in venture?
4.) How do Bill and Howard evaluate the state of the public markets today? Why does Howard believe that FOMO has really taken effect? How does Bill think about network effects and the laws of compounding with regards to public companies?
5.) Do Howard and Bill agree we are seeing a retreat from globalisation? What are the core impacts of this retreat? Why is Bill so concerned about "regulatory capture"? Why does Bill fear that today, "Washington is for sale"? What would he like to see change?
Item’s Mentioned In Today’s Episode
Howard’s Favourite Book: Across That Bridge: A Vision for Change and the Future of America
Bill’s Favourite Book: How Innovation Works
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Quentin Clark is a Managing Director @ General Catalyst, one of the most prominent firms of the last decade with a portfolio including Stripe, Airbnb, Snap, Anduril, Deliveroo and Cazoo to name a few. As for Quentin, at GC he has led deals in the likes of Kernel, Coda, Commure just to name a few. Before entering the world of venture Quentin was the CTO @ Dropbox and before that he was the Chief Business Officer @ SAP. Finally, before SAP, Quentin spent an incredible 20 years at Microsoft in a variety of different roles play a key part in their hyper-growth.
In Today’s Episode You Will Learn:
1.) How Quentin made his way from CTO @ Dropbox and 20 years at Microsoft to being an MD with General Catalyst today?
2.) What were Quentin's biggest management takeaways from his 20 years at Microsoft? What is his favourite story about working with Bill Gates? How does Quentin think about the art of delegation? How does Quentin differentiate between leadership and management?
3.) How does Quentin believe the world of fundraising has changed with COVID? How does Quentin build relationships of trust in these compressed fundraising timelines? What works? What does not work? How can you really build that relationship off Zoom? How does this change the fundraising landscape moving forward?
4.) What does Quentin mean when he says he likes to "lead without authority"? How does that translate into his management style? How does Quentin evaluate his style of board membership? How does Quentin know whether to wear the investor vs the operator hat on the board?
5.) Does Quentin believe we are really moving the needle in terms of the projects that venture is funding today? What would Quentin like to see more of? What would Quentin like to change about the world of venture? How does Quentin evaluate market timing risk when investing?
Item’s Mentioned In Today’s Episode
Quentin’s Favourite Book: Stranger in a Strange Land
Quentin's Most Recent Investment: Sprout Therapy
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Avlok Kohli is the CEO of AngelList Venture which has facilitated the funding of over 5,000 startups including 47 unicorns and is home to 4,300 funds and syndicates with $2.2B in assets under management. This year, AngelList Venture launched the much-discussed, Rolling Funds and Avlok recently launched his own rolling fund, Avlok Capital. Prior to AngelList, Avlok built and sold two companies; FastBite, acquired by Square in 2015 and Fairy, also acquired. If that was not enough, Avlok is also an angel in 25 companies.
In Today’s Episode You Will Learn:
1.) How Avlok made his way into the world of facilitating over $2Bn in AUM having sold 2 prior companies on the other side of the table as a founder? What is Avlok's favourite Jack Dorsey story?
2.) Why does Avlok believe Rollings Funds are the "printing presses of innovation" for capital markets? Does Avlok believe that everyone should be a fund manager and managing capital? What are the benefits of rollings funds vs traditional micro funds?
3.) How does the rise of rolling funds impact the early stage pricing of companies? How does it impact the competitive landscape for seed and pre-seed allocations? Is Avlok concerned about a wave of undisciplined capital entering the market?
4.) How does Avlok evaluate reserve allocations for early stage and micro fund managers today? What does the data show for funds that do reserve for pro-rata vs those that do not? How has this impacted Avlok's own approach to pro-rata and reserve deployment?
Item’s Mentioned In Today’s Episode
Avlok’s Favourite Book: Meditations
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David Hsu is the Founder & CEO @ Retool, the company that allows you to build internal tools, remarkably fast. David has raised over $69M with Retool from the very best in startups including Sequoia, YC, Patrick and John @ Stripe, Henrique & Pedro @ Brex, Paul Graham, Nat @ Github, Peter @ Segment, Tomer @ Gusto and Elad Gil to name a few incredible names. Today Retool works with some of the biggest companies in the world from Amazon to Volvo to Mercedes Benz.
In Today’s Episode You Will Learn:
1.) How David made his way from studying philosophy at Oxford to creating one of the valley's hottest companies in the form of Retool?
2.) How does David analyse pivots today? How does one balance between vision and persistence vs realism and knowing when is the right time to pivot? How did a conversation with John Collison change the course of Retool? What advice does David have for founders on pivoting?
3.) Why does David believe that YC is useful pre-product-market fit but useless post-product-market fit? What elements are so helpful vs not about YC? Why did David raise his Series A as a split between Sequoia and prominent angels? Why was that transformational for the company?
4.) Why was David sceptical of VCs for a long time? Why does David believe VCs are useless pre-product-market fit and useful post-product-market fit? What have been David's biggest takeaways from working with Bryan Schrier @ Sequoia?
5.) Why does David believe that once you are profitable and growing it is actually quite hard to become unprofitable? How does David advise founders considering raising VC vs bootstrapping? How does David know when to allocate resources more aggressively to a segment? What are the signs?
Item’s Mentioned In Today’s Episode
David’s Favourite Book: Godel, Escher, Bach: An Eternal Golden Braid
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Dylan Field is the Founder & CEO @ Figma, the company that helps teams create, test, and ship better designs from start to finish and is one of 2020's fastest-growing companies. To date, Dylan has raised over $132M with Figma from some of the best including Sequoia, a16z, Index, Greylock, Founders Fund and Kleiner Perkins. Figma's latest round valued them at a reported $2Bn. Prior to founding Figma, Dylan enjoyed internships at Flipboard, LinkedIn and O'Reilly Media.
In Today’s Episode You Will Learn:
1.) How Dylan made his way from an internship at O'Reilly Media and a Thiel Fellowship to founding Figma, one of the fastest-growing unicorns?
2.) How does Dylan feel about the future of education? What core questions do students need to ask before entering? How does Dylan assess the impact of the Thiel Fellowship today? Why does Dylan believe that everyone should be an intern? What did he take from that experience?
3.) How would Dylan describe his leadership style today? How has it changed over time? How did he get past micro-managing in the early days and learn to delegate? How does Dylan think about insecurity and vulnerability as a young leader today?
4.) What does Dylan foresee as the biggest challenges in Figma's transition from application to platform? How does Dylan evaluate the success of the Figma plugin ecosystem? How does Dylan think about the right cadence to roll out new products? How does Dylan think about catering to power users vs catering to the standard everyday user?
5.) What have been the most significant impacts of COVID for Figma? Why did Dylan choose to adopt a hybrid model for Figma in terms of working styles moving forward? What have been Dylan's biggest lessons of what it takes to attract the very best talent? What works? What does not?
Item’s Mentioned In Today’s Episode
Dylan’s Favourite Book: Snow Crash
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Johnny Boufarhat is the Founder & CEO @ Hopin, one of the fastest-growing companies on the planet, providing an online events platform where you can create engaging virtual events that connect people around the globe. In the last 13 months, Johnny has raised over $174M for Hopin from the likes of Accel, IVP, Slack, Northzone, Coatue, Salesforce and of course, 20VC Fund. With the funding, again in just 13 months, Johnny has grown the team from 10 people to over 210 people in 37 countries. In October of this year, Semil Shah awarded Hopin the label, "The Breakout Tech Startup Of 2020".
In Today’s Episode You Will Learn:
1.) How Johnny made his way into the world of startups and how severe health challenges led to his realisation and founding of Hopin?
2.) What have been Johnny's biggest lessons scaling the team from 10 to 235 in just 12 months? What starts to break and when? What does Johnny believe are the 3 stages of startup growth? What have been Johnny's learnings on what it takes to acquire the very best talent?
3.) Why does Johnny believe that remote has so fundamentally changed the game? How does remote culture differ from physical culture? What advice does Johnny have for those shifting from physical to remote? Where does Johnny see so many make mistakes with the remote model?
4.) Why does Johnny believe fundraising is a game of leverage? How does Johnny advise founders to structure their raise? Should they shop their term sheets around? Should founders always be raising? How should they think through a pre-emptive round? How does COVID change the world of fundraising?
5.) What does the world of virtual events look like in a post COVID world? What events will remain virtual? What will not? How does Hopin expand beyond purely events into the much wider "connection" space? How does that look both from M&A and product expansion?
Item’s Mentioned In Today’s Episode
Johnny’s Favourite Book: Nineteen Eighty-Four
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Reid Hoffman is a Silicon Valley stalwart in the modern technology world. On the investing side, he is a Partner @ Greylock, one of the leading venture firms of the last 2 decades with a portfolio including Facebook, Airbnb, Dropbox, Figma, Appdynamics and Okta to name a few. Reid has led investments in Airbnb, Convoy, Coda and Aurora to name a few. As an operator, Reid co-founded LinkedIn, the world’s largest professional network and before LinkedIn, Reid served as executive vice president at PayPal, where he was a founding board member. If that was not enough, Reid is the co-author of Blitzscaling and two New York Times best-selling books: The Start-up of You and The Alliance.
In Today’s Episode You Will Learn:
1.) How Reid made his way into the world of startups, came to found Linkedin and how that led to his joining Greylock?
2.) Does Reid consider himself an innate and natural leader today? How has his leadership style changed over time? What elements does Reid struggle with? How has he scaled to these leadership challenges? What does Reid believe are the different strands of leadership?
3.) How does Reid think about what separates the good from the great board members? What is the biggest danger for board members today? How do the very best founders manage their boards? How does Reid think about the weight of his words today?
4.) How does Reid think about the importance of ownership? How does Reid analyse price today? What was the story behind Greylock investing in Airbnb? What did Reid see so clearly and before anyone else saw it? What is the story with Stripe? Why did Reid turn Stripe down?
5.) How does Reid think about ensuring venture partnerships always have a learning mindset? What can be done deliberately to ensure this? Where do many people struggle here? How can partners develop trust within venture partnerships? Where does trust most often break down?
Item’s Mentioned In Today’s Episode
Reid’s Favourite Book: Thinking, Fast and Slow, Amusing Ourselves to Death: Public Discourse in the Age of Show Business
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