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The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

The Twenty Minute VC takes you inside the world of Venture Capital, Startup Funding and The Pitch. Join our host, Harry Stebbings and discover how you can attain funding for your business by listening to what the most prominent investors are directly looking for in startups, providing easily actionable tips and tricks that can be put in place to increase your chances of getting funded. Although, you may not want to raise funding for a startup. The Twenty Minute VC also provides an instructional guide as to what it takes to get employed in the Venture Capital industry, with VCs giving specific advice on how to get noticed from the crowd and increasing your chances of employment. If that wasn't enough our amazing Venture Capitalists also provide their analysis of the current technology market, providing advice and suggestions on the latest investing trends and predictions. Join us so you can see how you can get BIG, powerful improvements, fast. Would you like to see more of The Twenty Minute VC, head on over to www.thetwentyminutevc.com for more information on the podcast, show notes, resources and a more detailed analysis of the technology and Venture Capital industry.
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Now displaying: 2021
Mar 29, 2021

Peter Fenton is a General Partner @ Benchmark, one of the great venture firms of the last 3 decades with a portfolio including the likes of SNAP, Twitter, eBay, New Relic, Stitchfix and many more. As for Peter, he has led deals, sits or has sat on the boards of Elastic, New Relic, Digits, Docker, Optimizely, Yelp and Zuora to name a few. Prior to Benchmark, Peter was a General Partner @ Accel Partners in San Francisco. As a result of his incredible track, Peter has been on the Forbes Midas List more times than I have done podcast episodes!

In Today’s Episode with Peter Fenton You Will Learn:

1.) How a round of golf led to Peter Fenton leading the New Relic Series A? What did the deal look like both in check size and valuation? What does Peter think that round would be in today's market?

2.) How does Peter create an environment of safety with entrepreneurs where they feel they can be vulnerable with him? How does Peter approach building relationships of trust in compressed fundraising timelines? In what way has Peter seen relationships go bad? What can been done to mitigate that and optimise the Founder <> VC relationship?

3.) How does Peter assess market timing when making investments today? What does Peter mean when he says, "you have to understand whether you are unlocking consumption"? What does unlocking consumption look like in reality? How does Peter think about positive or negative externalities that could impact the business?

4.) Does Peter agree with Bill Gurley that the biggest challenge today is the "oversupply of capital"? Where does the oversupply of capital become a real challenge? What does Peter advise growth-stage founders do to prevent this from damaging them? How does Peter think about capital efficiency in the companies where he is on the board?

5.) What were Peter's biggest lessons on what it takes to be a great board member from his 12 years at New Relic? How did he see his style of board membership change? On the founder side, how do the very best founders manage and navigate their board? What do most boards misunderstand or mismanage?

Item's Mentioned In Today's Episode with Peter Fenton

Peter's Favourite Book: Nonviolent Communication: A Language of Life

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.

Mar 26, 2021

David Velez is the Founder & CEO @ Nubank, one of the fastest growing digital banks in the world with operations in Brazil, Mexico, Argentina and Colombia. To fuel this growth, David has raised over $1.5BN for Nubank from some of the best in the business including Doug Leone @ Sequoia, Micky @ Ribbit, Thrive, Founders Fund, DST, Tiger and more. Before changing the world of LATAM finance, David was a Partner @ Sequoia where he was responsible for all LATAM investments. Prior to Sequoia, David was the co-founder of General Atlantic's South American investment programme.

In Today’s Episode You Will Learn:

1.) How David made his way into the world of startups through becoming a Partner @ Sequoia? How that led to his founding of Nubank? How his time at Sequoia impacted how he thought about building Nubank?

2.) How does David think about the relationship between growth and quality in company scaling? When scaling so fast, what are the first things to break? How does one know when is the right time to expand geographically? What is the right thought process to go through when determining how to know when is the right time to expand product lines?

3.) Looking at the market today, how does David for-see the future of digital banks? Will we seen increased consolidation over the coming years? How does David think through the verticalisation of neo-banks? What does the reduction in barriers to creating neo-banks really mean? How did Nubank scale to the scale it is today with $0 CACs?

4.) How has David seen his leadership style change with the growth of the company? Why does David feel it is wrong that the titles of Founder & CEO are so inextricably linked? What element of being a great founder are actually not good for CEOs to have? What elements of great CEOs are bad for founders to have? What has David found the hardest to scale in himself?

5.) How does David use "the responsibility framework" when making decisions today? What are David's thoughts on imposter syndrome within leaders today and how it can be harnessed for good? How does David approach head vs heart when it comes to decision-making today? Does David engage with regret minimisation as part of this?

Item’s Mentioned In Today’s Episode

David’s Favourite Book: One Hundred Years of Solitude

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.

Mar 24, 2021

Jeremy Levine is a Partner @ Bessemer Venture Partners, one of the leading venture firms of the last 2 decades with a portfolio including the likes of Pinterest, Shopify, LinkedIn, Yelp, Twilio and many more. As for Jeremy, five of his early-stage investments—LinkedIn, MindBody, Pinterest, Shopify and Yelp—grew into billion-dollar publicly traded companies. As a result of his incredible portfolio, he has featured on the Forbes Midas List for several years running.

In Today’s Episode with Jeremy Levine You Will Learn:

1.) How Jeremy came to make one great decision and make one big mistake all in one rainy afternoon in Palo Alto? What was the story behind meeting the Pinterest team for the first time? Who was there? How did it go down?

2.) Market: How did Jeremy analyse the market at the time of the investment? What had been some core lessons Jeremy had learned on what made successful user-generated content plays? Where was Jeremy wrong in how he analysed the market? In what way is Jeremy surprised with how the market evolved? How does Jeremy analyse market timing today?

3.) Team: Jeremy has previously called Ben Silberman a "product visionary", what made Jeremy say this about Ben? How did Jeremy get over the concern of many VCs that Pinterest did not have a technical co-founder? Having seen Ben change over the last decade, what have been the biggest changes in Ben's leadership style over the last 10 years?

4.) Traction: When evaluating traction, where does Jeremy think so many investors make mistakes today? How should founders determine what is their core North Star metric? What gave Jeremy the confidence Pinterest could "cross the chasm"? How did the early Pinterest cohorts look both from usage and retention? What elements surprised and impressed?

5.) Pre + Post Mortem: What did Jeremy see as the likely reasons why Pinterest would not work? How did Jeremy think through what it took for UGC platforms to monetise at the time? Where was he wrong here? What did Jeremy see as the upside? What did he believe Pinterest could be if all the stars aligned?

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.

Mar 22, 2021

Jason Fried is the Founder & CEO @ Basecamp, the project management and team communication tool trusted by millions. Over an incredible 22 year journey, they have scaled to over 3.5M accounts and in 2020 they went back to being a multi-product company with the launch of their integrated email client & service, HEY. Jason is also the co-author of the widely acclaimed, ReWork and has also made several angel investments in the likes of Intercom, Gumroad and Hodinkee to name a few.

In Today’s Episode You Will Learn:

1.) How Jason Fried made his way into the world of startups and came to found one of the leading project management and team communications tools in the form of Basecamp?

2.) How does Jason analyse and evaluate his relationship to money? Why does Jason believe that he has this inherent downside protection when it comes to money? How does he structure his personal finances between stocks, cash, crypto etc etc? What have been some of Jason's biggest lessons when it comes to tying happiness to monetary levels?

3.) What does Jason mean when he says, "I have a fantasy of getting fired"? How does Jason think about knowing when is the right time to step away from the business? What would he like to do with that time? How does Jason feel about the challenge of tying his identity to his company? What are the dangers of doing so?

4.) How does Jason approach decision-making frameworks? What does Jason believe is the right way to respond when a decision does not go as planned? Where do many make mistakes here? Does Jason feel regret with decisions? How does Jason try and minimise regret?

5.) How does Jason feel about his biggest insecurities as a leader and CEO today? What are Jason's views on a CEO's ability to have self-doubt and be vulnerable? How have his views on this changed over the years? In what way has having kids impacted Jason's operating mindset? How has it changed what he values and appreciates?

Item’s Mentioned In Today’s Episode

Jason’s Favourite Book: In Praise of Shadows

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.

Mar 18, 2021

Simón Borrero is the Founder & CEO @ Rappi, the startup that has become a cornerstone of the Latin American mobile ecosystem, coined as "the next Everything Store of Latin America". To date, Simon has raised over $1.7Bn for the company from the likes of Sequoia Capital, a16z, Softbank, DST Global, Y Combinator and more. Prior to Rappi, Simon was the founder of multiple former companies including Imaginamos, a software studio he grew to over 300 people.

In Today’s Episode You Will Learn:

1.) How Simon made his way into the world of startups and came to found "the next Everything Store of Latin America" in Rappi?

2.) How does Simon think about the importance of zone density for a business like Rappi? What are the number of deliveries required for Rappi to make for the business to be breakeven? What is the key metric that determines the success of the business for Rappi today?

3.) How does Simon approach the balance of capital efficiency vs growth? How does one know when to pour fuel on the fire and go for growth? When is the right time to really focus on unit economics? Why does Simon believe expanding Rappi can be analogised to scaling a coffee shop?

4.) Rappi has now raised $1.7Bn from some of the best investors in the world, what does Simon believe Rappi did to enable them to be so successful fundraising? Was it a difficult shift for Simon to make moving from lean to capital abundance with the successful fundraises? What changed? How did Simon change as a leader? What is the story of Sequoia coming in?

5.) Customer acquisition: What were some of the biggest challenges when it came to initial customer acquisition for Rappi? What does Simon mean when he says "donuts for downloads"? What is the story there?

6.) Driver acquisition: In the UK and the US, driver acquisition is a big challenge, what did Rappi to do enable them to scale their driver supply so efficiently? What works? What does not work?

7.) Restaurant acquisition: What were the hardest elements of onboarding the first restaurants? How did Uber Eats entering the market actually make Rappi so much more efficient as a business and service?

Item’s Mentioned In Today’s Episode

Simon’s Favourite Book: The Prosperity Paradox

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.

Mar 15, 2021

Tony Fadell, often referred to as “the father of the iPod,” is currently Principal @ Future Shape, a global investment and advisory firm coaching engineers and scientists working on foundational deep technology. Prior to Future Shape, Tony was the Founder & CEO @ Nest Labs, the company was ultimately acquired by Google for a reported $3.2Bn. Before Nest, Tony spent an incredible 9 years at Apple Inc, where, as SVP of Apple’s iPod division, he led the team that created the first 18 generations of the iPod and the first three generations of the iPhone. Fun facts, Tony has filed more than 300 patents for his work and is also a prolific angel investor having invested in the likes of mmhmm and Nothing to name a few.

In Today’s Episode With Tony Fadell You Will Learn:

I. The building blocks of an entrepreneur

What was the moment that Tony realised that he wanted to be an entrepreneur?

“I got my first money when I was in third grade, because I had an egg route. We'd go get eggs from the farmer, and I'd load them in my wagon. Then my younger brother and I would go door to door around the neighborhood, and we'd sell eggs. And that was an every week or every other week situation. And I got money in my hands. And I was like, Oh my God, I can do whatever I want with that money – I don't have to ask anybody, I can just do it. And so that was the level of freedom that, especially when you're young, feels really cool. And then as I got older, I started to buy Atari video game cartridges for my 2600 (yes, I'm that old!), and that was really, really fun too.”

What was the biggest lesson that Tony learned from his father on sales and building trusted relationships?

"And he said, very clearly, Look, this is a relationship. If I make this person successful, he's gonna want to come back to me over, and over, and over. But if I sell him something and it doesn't sell, and he has to discount and he loses money, he's not going to come back. Even if I don't have the right product, I'll tell him where to go to get the right product they're looking for, or if they're picking the wrong one, I'll tell them, here's the right one, because my job is to make them successful. Because if they're successful, they'll come back to me year after year after year. And even when we have a down year, they're going to trust me, and they're going to come back."

II. Reflections on experience

How does Tony Fadell think about and assess his own relationship to money? How has it changed over the years?

"So my relationship to money now is that it's just a means to make change happen. And so literally, for me, I can just have a backpack, my computer, my phone, a couple of roller bags with my clothes. And that's enough to live life with my family. I don't need all this other stuff. COVID taught me that even further."

How does Tony determine true friendships vs transactional relationships?

“If it's not a reference – if it's not coming from somebody saying, Hey, you really need to meet this person – I take everything with a grain of salt. With anybody who comes to me cold, I think they probably want something. I try to find that out through the network, Do you know this person? What are they about?"

III. Tony Fadell on becoming a mentor

Why does Tony Fadell believe that founders have to be "coachable"?

“I think anybody who's trying to do something that the world has never seen before, or trying to work with people who are, they'd better be coachable. Because you're going to be so narrowly focused, you're going to be so heads down, you're going to be so on a mission, that sometimes you'll be blinded, and you'll need somebody to come from left field and go, Wait a second, dude, you're not thinking about this right."

What are the core signs that an individual is coachable?

  1. Trustworthiness

2. Willingness to listen

What does Tony believe is the right way to deliver advice without fluff?

"First, it's about trust. You have to be able to have a trusted relationship with somebody. And second, there are different ways of delivering a message. You can deliver a message the first time in an iron-fist-in-a-velvet-glove kind of way. But sometimes the velvet glove is going to come off."

How do people make mistakes when giving advice?

“I'm in too many board meetings; we have over 200 investments. I've seen all kinds of different CEOs and different boards, where the investors don't want to feel like they're going to get a bad rep because the CEO is going to say something if they say something negative."

What does Tony Fadell advise founders when it comes to finding mentors?

“Usually, a really great mentor is going to be highly selective. They're going to be like, I don't want to work with you. They only have so much time for people who are actually coachable."

What are the characteristics of the best mentors?

"You're gonna have tough love with them, you're gonna say things that they don't want to hear, you're not going to be liked all the time. Hopefully, one day, you'll be respected if not liked. And that's what it means to be a mentor.” 

IV. Changing perceptions

How does Tony assess his own relationship to self-doubt?

“Everyone goes through imposter syndrome. Everyone does. We all have gone through it, I go through it. Because you know what, when you're doing stuff you've never done before, and you're changing the world, no one else has done it either. No one else has done it either. That means it's okay. And I always say, if you don't have butterflies in your stomach each day, you're either not paying attention, or you're not pushing hard enough and taking enough risk."

What are Tony's views on failure?

“Now, there's taking stupid risks versus risk mitigation and taking calculated risks. But you should always be living on the edge of pushing yourself because that's where the growth is, that's where the change is happening."

Does one learn more from success than from failure?

"How we do and change the world is through the same method. We go do, and then we fail, and then we learn from that, and then we do again.”

What does Tony mean when he says, "do, fail, learn."

“Look, it's do, fail, learn; do, fail, learn. There's no such thing as learn and then you're able to do. No, no, no. When you really learn in life is after you've tried to do it."

What is the right way for entrepreneurs to present their boldest of ambitions?

"Look at Elon now. If he was pitching what he's doing now 15 years ago, people would go, No way! A few people, like Jurvetson and others, said, Yeah, sure, okay, great. But very few people would get behind that huge boldness."

“So what they do is – and this is what I've had to do – they start and just pitch that simple ‘What's the next three to four years look like?’ and never tell anybody about the big picture. Because you scare most people off."

How do investors need to change how they think about ambition and upside?

5.) Why does Tony believe the first trillionaire will originate from the climate change space? Why is the majority of plastics recycling total BS today? Why does Tony believe we need to fundamentally transform our economies? How do funding markets need to change to fund this structural reshaping of society?

Mar 11, 2021

Scott Sandell is the Managing General Partner of NEA, one of the leading firms of the last 3 decades with now close to $24Bn under management and a portfolio including the likes of Salesforce, Robinhood, Plaid, Databricks and many more incredible companies. As for Scott, since joining the firm in 1996 he has led investments in many industry-transforming technology companies including Salesforce.com, Tableau Software, WebEx and Workday. Scott also serves on the board of rocketships including Robinhood, Cloudflare, Coursera and Divvy to name a few. As a result of this investing success, Scott is among the most frequently named venture capitalists to the Forbes Midas List.

In Today’s Episode You Will Learn:

1.) How Scott made his way into the world of venture close to 3 decades ago back in 1996? How he came to be Managing General Partner of NEA today? What is entailed in the role of "Managing General Partner"?

2.) What has been the single biggest change in the venture landscape that Scott has observed since his entering in 1996? How did the boom and bust of the dot com and 2008 impact his investing mindset? Consequently, how does Scott advise founders to think about capital efficiency and business model flexibility? What concerns Scott today?

3.) Why does Scott believe "this is an incredible moment in history for the asset class of venture"? How does Scott think about the core physics of company building changing? How is it companies are able to scale and grow so much faster today? Does their speed of growth change their capital requirements?

4.) Does Scott agree with Bill Gurley, "the biggest challenge is the oversupply of capital today"? How does Scott analyse his own relationship to price and price sensitivity? What is Scott's framework for determining when to pay up vs when to remain disciplined? How does Scott feel about the rise of SPACs? How will this shake out over the coming years?

5.) How much have NEA companies raised over the last decade? Of that, how much did NEA invest? Is the answer to continuously scale AUM? How does NEA approach investment decision-making with the size of partnership it has? What does Scott mean when he says, "we vote on the process"? How do you create a partnership of trust at scale?

Item’s Mentioned In Today’s Episode

Scott's Favourite Book: The Old Man and the Sea

Scott’s Most Recent Investment: Loanpal

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.

Mar 8, 2021

Daniel Ek is the founder, Chief Executive Officer, and Chairman of the board of directors of Spotify, the world’s most popular audio streaming subscription service with 345m users, including 155m subscribers, across 170 markets.

In Today’s Episode With Daniel Ek You Will Learn:

1.) How Daniel made his way into the world of startups and came to found the most popular audio streaming subscription service in the world in the form of Spotify?

2.) How does Daniel approach effective decision-making today? What is his core process? How does Daniel determine between reversible and irreversible decisions? What does Daniel's learning process look like for new topics and material? How does this differ from topic to topic? What does Daniel mean when he says "I look to become the Chief of X Officer" for a time?

3.) How does Daniel think about the transition from Founder to CEO? Why is the topic not discussed enough? Where does Daniel see many founders struggle to make the transition? Which elements did Daniel find the most challenging? How has he scaled into them over time? Is it possible to change who you are as a person with this transition?

4.) How does Daniel think about what it takes to create an environment of safety where everybody can feel free to express their ideas, thoughts and concerns? What sort of failure does Daniel accept? What sort of failure does Daniel not accept? How does good news flow through an organisation differently to bad news? How does Daniel determine when to quit a project vs when to persist and stick to it?

5.) Prima Materia: Why is Prima not just another fund? How is Prima fundamentally different? What does Daniel believe Shak is world-class at? A walkthrough of Shak and Daniel's decision-making process for choosing to partner with each other on Prima? What has been their first investment? Why gave them the conviction to write this check as their first?

Item’s Mentioned In Today’s Episode with Daniel Ek

Daniel’s Favourite Book: Shantaram

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here.

Mar 4, 2021

Vlad Tenev is the Founder & CEO @ Robinhood, the company that provides commission-free investing, plus the tools you need to put your money in motion. To date, Vlad has raised over $5.6BN with Robinhood including a $2.4Bn raise this month and some of their investors include the very best in the business; Ribbit, Sequoia, Greenoaks, Index, IVP, Thrive, GV and more incredible names. Before Robinhood, Vlad started two finance companies in New York City.

In Today’s Episode You Will Learn:

1.) How Vlad made his way into the world of startups and how the "Occupy Wall St" movement spurned much of the inspiration for the founding moment of Robinhood?

2.) Looking back over the last month, does Vlad believe Robinhood is a victim or an enabler of the crisis? What does Vlad believe upset customers the most? With the benefit of hindsight, what would Vlad have done differently? What does Vlad believe are some of the biggest misconceptions about how the last few weeks played out?

3.) Funding: Why did Robinhood need the scale of funding that it took, so fast? What are the capital requirements for a business like Robinhood? Who regulates their compliance? Was Robinhood forced to put the interests of the business ahead of the interests of their customers? Why does VAR need to be changed as a risk estimation mechanism?

4.) What has Vlad learned as CEO about managing through a crisis? What did Vlad do to ensure morale remained high internally, despite the external events? What works? What does not work? What did Vlad learn about himself through the experience of the congressional committee and testifying before them?

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.

Mar 1, 2021

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.

In Today’s Episode You Will Learn:

I. The Importance Of Learning To Learn Fast

What is the best way to learn fast? 

“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.” 

Does Sebastian compare his work to other companies’?

“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.” 

How does Sebastian transform his self-doubt into a positive?

“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.” 

II. Sebastian’s Management Philosophy

What does Sebastian believe companies can learn from soccer? 

“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.”

How do you know when someone is at that crucial point of the learning curve?

“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.”

III. How Sebastian Manages Complexity At Scale

What are Sebastian’s biggest lessons learned from Klarna growing to 3000+ people spread across multiple offices across the world?

  1. It’s the manager’s job to deal with the complexity in a company 
  2. It’s not for everyone 

What role does Sebastian believe a manager should play in a company as it scales?

“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.”

What does Sebastian look for in talent? 

“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.”

IV. Retail Banking 10 Years From Now

What does Sebastian see as the future of everyday banking services?

“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.”

What do the next five years look like for Klarna?

“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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Feb 26, 2021

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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Feb 24, 2021

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.

In Today’s Episode We Dissect The Snapchat Memo:

I. How Jeremey first learned of Snapchat

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."

II. The Analysis Of Snapchat's Early Market

What are the 4 things Jeremy looks for when making an investment in consumer?

  1. Can this become part of pop culture?
  2. Does this create new habits?
  3. Is there a scalable way to grow?
  4. Does the founder have a unique insight that explains the success?

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"

III. Reflections on Snapchat's Early Traction

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."

IV. The Truth About The Snapchat Founding Team

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."

Feb 22, 2021

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

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Feb 18, 2021

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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Feb 15, 2021

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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Feb 11, 2021

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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Feb 8, 2021

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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Feb 4, 2021

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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Feb 1, 2021

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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Jan 29, 2021

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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Jan 27, 2021

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?

As always you can follow Harry and The Twenty Minute VC on Twitter here!

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Jan 25, 2021

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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Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jan 21, 2021

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

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.

 
Jan 18, 2021

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

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.

Jan 14, 2021

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

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.

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