The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. If you would like to see more of The Twenty Minute VC (20VC), head to for more information on the podcast, show notes, resources and more.
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Dec 21, 2022

20VC: Fundraising 101

Today we are going to walk through the process of raising a funding round for a hypothetical company. We will break it down by different stages in the fundraising process and at those stages I will talk about how each element differs according to the round being raised. 

First, for 99% of fundraises it is a game of shots on goal. You need to have enough investors in the pipeline, it is a sheer numbers game. Miki Kuusi @ Wolt said on 20VC recently for his Series B he got 68 rejections before Laurel Bowden @83North said yes. Wolt sold in 2021 for $7BN to Doordash making a monster return for the company's investors. But 68 meetings before that yes, for the Series B. Also goes to show, you sometimes just need one true believer. 

How to Create a Target List of Investors

Now we know we need enough shots on goal, we need to bring together a target list of investors, put these investors in three buckets:

  1. Priority (5 names of people you really want.)
  2. Tier 2 (15 names of people you would like)
  3. Tier 3 (15 names of people you would take money from but would not invite to your birthday!) 

So how do we choose who goes in what bucket? First, founder references speak volumes and lead to warm intros, so speak to your friends who are founders, ask which of their VCs have been the best, place even more weight on their recommendation if the company has not been a success. It is easy to be a VC champion when the company is flying, you often see the true colours of the VC when a company is really struggling or fails. Get a couple of names there and then analyse the VC landscape, you can do this on Twitter or the VCs website or blog and find the VCs that resonate best with your company. Look at the types of deals they have done before, are they interested in pre-seed fintech in Europe, do they do enterprise SaaS Series A in the Silicon Valley. You can see their portfolio, make sure it is a fit for them. I get about 200 inbounds per day across channel, about 150 are clearly not a fit for me because of stage, sector or location and so making sure the obvious are aligned is crucial. Then double down on their Twitter or public profile to see as much as you can about their values and how they portray themselves. Rule No 1, never work with assholes. Value alignment is really important. Now we have the five priorities and then I would say do the same for the Tier 2 and Tier 3 bucket, make sure they invest both in your stage, sector and geography. 

The Biggest Mistakes Founders Make Pitching:

So now we have our pipe of investors. A couple of big mistakes I see founders make in this next step. 

  1. They go to their priority names first. Do not do this. Your pitch both in delivery, style and messaging will improve so much with each meeting. Start with a couple where you would not be sad if they said no. Analyse in real time in those meetings what messages are hitting and what are not, where are investors spending the majority of the time, are there common questions that keep coming up. If so, create an FAQ page that is in the deck and that will prevent you from having to answer the most obvious in other meetings. With each meeting, you will find ways to iterate the deck, the messaging and the way you present. 
  2. Another massive mistake founding teams make, if you are doing a Zoom call and it is a first meeting, do not have more than 2 people on the call from your team. It makes it tough to get to the core of the discussion and removes a lot of the relationship building with too many people too soon. If the investor likes the opportunity, they will ask to meet more team members but do not put too much in front of them to the point it dilutes the message and pitch. 

Now we have done the first investor meetings and we have iterated our deck and messaging in accordance with the feedback we got. We now progress to taking meetings with investors we want as our partners. 

How to Master the Subtleties of a First VC Call:

  1. Every investor call usually starts with each side telling a little about themselves and how they came to be the founder or the VC. As the founder, practice your intro, make it succinct, concise, break it into three chapters, a minute per one is a good guidance. In these you want to show a couple of things, founder <> problem fit or in other words, why you specifically have the right experience or skills to attack this problem. I also like to understand “insight development” as taught to me by the famous OG of seed investing, Mike Maples @ Floodgate. Insight development is the notion that the best companies are founded on a unique insight that the founder has about a product or market that is different to the way the world currently sees it. Include these two in your intro. Keep the intro to no more than 3-4 mins. 
  2. For the VCs intro, it is important to try and understand a little more about them. Many VCs give boring and bland intros; “we do Series A and B in Europe and like to lead rounds.” Very standard response and so you should ask them how they like to work with their founders, ask them about a company that struggled and how they worked with the founder to help. Ask them about their decision making process for reserves and pro rata. This creates more of a conversation which will instantly give you as a founder more gravitas in the eyes of the VC. 
  3. Use the deck as a vitamin and not a painkiller. I hate pitches where it is read off slide by slide. I would not have the slides showing at all, I will have asked for a deck pre the meeting and I should have gone through it before. The call is for me to ask about questions I want to understand more or double click on. That said, the deck can often be useful as a crutch and so it can work well to have it ready and refer to certain slides as and when necessary. 


The 7 Sins of Fundraising Decks:

So while we are on the deck, I want to go through a couple of elements that I so often see and they are killer mistakes:

  1. Length: Keep the deck less than 10 slides. If you need a couple more to show data or additional research, put it in the appendix at the end of the deck. 
  2. Introduction: First slide, company name and then answer the question; if I had a billboard in Times Sq, what would it say on it? 10 words max. From your first slide alone, there should be no doubt about what your company does. 
  3. The Team Slide: where do people go wrong here. They put 12 faces on it with their names. No information about the people, where they worked, why they are the best team to solve this problem. A totally useless slide if done like this. So do not do this. Instead, take 4 of those people, break the slide into quadrants and expand on those 4 people’s backgrounds to why they are perfectly suited to do what they are doing. Fewer people more context. 
  4. The Useless Advisor Slide: Aligned to the terrible pictures of many team members with no context, the advisor slide, honestly, advisor slides just carry such little weight these days, they are not worth having. Take it out, it is not needed. 
  5. Market Sizing Errors: This is a massive one. I see so many make the mistake on market size slide. Say we have a CRM for hairdressers, taking a very random example here, so often I will see a $100BN market, thats the TAM for the hairdressing market or the CRM market, but we are CRM for hairdressers so that is not the right representation and is entirely misleading. It is much better to start with that, then show the slither of wallet spend that hairdressers spend on software and then show the even smaller slither that they spend on CRMs. Use the market sizing slide as a way to show your insight and intellect both into how the market is carved up today but also how it is going to change in the future. There is always the debate of what matters more, large market or amazing founders, the truth is, a massively growing market can cover a lot of operational sins and so showing how the market is and will expand and what causes this, the why now, will always be important. But do not show the massive market for hairdressing or whatever it is, I have seen more $1TN TAM for pet grooming businesses that you can imagine. So do not do that. 
  6. Exit Slides are Terrible: I do not see this so often now but do not have an exit slide in the deck for your early stage company, the wrong type of investors will be attracted to you if they like this slide, it encourages short term thinking and is not the right way to present for a company that will reshape an industry so no exit slide. 
  7. Why You Should Not Invest: One thing I love in startups and always have when I present my funds is a slide, why you should not invest in me. I think the most important thing for all founders is to be aware of their biggest weaknesses and then have clear action plans on what they are doing to mitigate the chances of them impacting their success. So have a slide that says, hey, these are our 3 biggest weaknesses and then tied to each one, this is what we are doing to solve it. This inspires trust in the relationship with the investor and really shows your self-awareness and strategic thinking.

How To Structure The Size and Composition of Your Funding Round:

Now at some point in the discussion the size of the round and the price of the round will be asked. Use this as a chance to show your calibre as a founder. 

  1. You Cannot Sit With Us (You Get The Joke!!!): Massive mistake founders make is they structure a round that does not allow for a VC to invest. What do I mean by this? VCs that lead rounds need to own at least 8% very minimum and if you come in raising $2M on a $25M cap, that is not enough allocation for the VC and pro-rata amount and then angels as well. Do not prohibit the VC from investing because of the structure of your round. For that example, $5M on $25M would allow for the VC to have 12.5% ownership, a smaller fund to have 3-4% and then a 3-4% allocation for angels. 
  2. Is This Check Meaningful?: An important question to ask is: is the check size being invested by the lead a material check size for them and their fund? For example, if the check size they are investing is less than 1% of their fund, it is not that meaningful, if it is less than .5%, it really is not meaningful. Now this could be bad as it means they are unlikely to be able to provide you with the same time and attention they would larger checks. That said, Jason Lemkin has also commented before on the benefits of this as they will leave you alone to execute, they will not put much pressure on you as you are not a core position and it is really yours to execute from there. 
  3. Do Not Do a Range: In terms of the actual size of check being raised, I do not like ranges. There is a massive difference between 3 and 5 million, and that impact on your runway is huge and so state a clear and direct number you are raising and what runway that will provide. 
  4. Milestone Hitting and Showing Resource Allocation: Use the question of how much are you raising to show your insight into the milestones that you need to hit over the next 18-36 months. Never raise less than 18 months, you also do not need to raise more than 36 months. Plan for a 6 month fundraise and execution 99% of the time always takes longer than you anticipate. With that in mind, I always prefer 24 months as the right period to raise for, this will give you 18 months heads down execution and then 6 months to raise. 
  5. Fundraising Rounds are To Prove Hypotheses: If we assume that fundraising rounds are science experiments and you have to prove or disprove a set of hypothesis with this time and money, make sure you can clearly articulate what you need to prove and by when. For the love of god do not say, this is the last round we will ever need to raise before we are immensely profitable, I could have a fund the size of Softbank if I had a dollar for everytime someone said that to me. 

How to Answer the Question of Valuation:

When you say the size of the raise, say $2M, the basic assumption is that each round will dilute 15-20% and so the average VC will think of a $10M post money valuation straight away when you say a $2M raise. That said, you do not want to anchor yourself to a price, you are running a process as transactional as it sounds and I am not saying you want to optimise for price by any means but the majority of the time, it is best to say, “hey we are raising $2M and we will let the market decide on the price”. This is a great way to answer the question as this will not put anyone off, it will not anchor you to a price and it will also show you are savvy as to the raise process which any incoming investor should want to see as your ability to raise the next round is fundamental for them. Again, use this question to show your sophistication and knowledge as to the finer details of how to navigate a fundraise successfully. 


How to Choose Your Lead Investor?


The biggest problem of the last 2 years was people chose their lead having met them once. They will be a partner to you for 10 years and you will not be able to get rid of them, it is literally harder to remove an investor than it is to get divorced. Brian Singerman @ Founders Fund said on the show recently about how he was unable to do his job in COVID as he could not meet founders in person. It is so important to meet your lead investor in person before signing the deal, so much can be gained and learned from those meetings in person. Then there is the question of how do I really get to know someone, especially if it is in a compressed timeline, there are ways that you can accelerate a relationship and getting to know someone, make sure to ask:

  1. What would success look like to them with this investment? What are the 1-2 core ways they believe that you will not achieve your outcome? What worries them?
  2. Can they give you a reference for founders they have worked with where it has not gone to plan? Also do off sheet references and try to find others where it did not go to plan. You can find their email with the Google Plugin by Clearbit and that is super easy. That should reveal alot. 
  3. I also find really being vulnerable, talking about ambitions, inspirations, fears, childhood, my mother has MS and it is a tough and horrible thing to see your mother suffer with, I will discuss that and how it has changed me and my mindset in many ways. 

How to Set a Timeline in a Fundraise?

In this deliberation phase where you are waiting for a term sheet, you do need to create some form of urgency. Investors often need a reason to move and so it is good to put a timeline on the raise. 14 days is perfect, this is enough time for any VC to do the work they need to do but also if they cannot do it in that time without a plausible excuse, it is unlikely that they would have done the deal and so it will force timewasters to a no sooner and save you time. 

Your Term Sheet is Ticking:

One thing to be wary of is exploding term sheets. If any VC says you have to sign this here and now, that is BS. Do not do it and that is no way to start a 10 year relationship. That said, it is fair for them to set some form of timeline, otherwise, you can shop the term sheet; share it with everyone and use the first people to commit as leverage to create FOMO to get other people to commit. This can be a disadvantage of being a first mover as a VC but that is why they will often have some form of expiry date and that is not unreasonable. 


When You Have Multiple Term Sheets: KISS (KEEP IT SIMPLE STUPID)


Then you have leverage and you can optimise the round on price, size of round, size of lead check to angel allocation etc etc. My advice here would always be do not over optimise. If the chosen partner is slightly lower, take it. Do not lose the right partner because of a small 5% difference in price or size of round. Another big mistake founders make when they have multiple term sheets is communication. It is fine if you need another couple of days to consider the decision but keep everyone updated. Let each investor who is waiting know, you are still thinking it through and will be back to them shortly. Name when you will have an answer, a communicated delay is fine, no communication is not. Then another massive mistake founders make is for the VCs they choose not to go with, they do not turn them down graciously. These investors could likely fund your next round, a bridge round and you never know when you might need them and so always turn them down super well and keep them on side, they could be helpful in the future.

If a VC Does These 3 Things: Forest Gump It: 

Now the massive red flags with leads in this process that we need to call out:

  1. Pay to Pitch: If any VC ever makes you pay to pitch them. This is unacceptable and we have to remove this from the industry. Tweet me the details of these investors, it can be anonymous but these bad actors need to be called out.
  2. Investment Tranches Kill Companies: If it is an early round and they want to do the investment in tranches. No. This is such an inhibitor for the business it will not allow you to allocate resources effectively or with confidence. Do not allow for tranches. A bad deal can sometimes be worse than no deal. Tranches does not set you up to execute against a plan, build a world class team and achieve what you can. Say no. 
  3. Early Signs of Excess Control and Ego: If they haggle immensely on salary over small amounts, if they suggest you should be on $60K not $62K and they make a big deal out of it. This is a sign of what they will be like to come. Do not accept it. 

So now we have our lead VC locked in and we have to allocate the rest of the round. I would work hand in hand with my VC to construct the rest of the round. They will have angels they work closely with and think highly of. Use them to help map out those people and then make those intros for you. 

How to Allocate Your Angel Allocation:

Assemble your angel cap table as you would a sports team. Each person has a specific position which they are specialised to and have a world class skill in. Someone for marketing, hiring, regulation, PR, partnerships etc. A massive mistake I see so often is founders try to cram down all their angels to their smallest allocation so they can fit as many as possible. Do not do this. Give fewer people more allocation. The only thing that matters is that the check size matters to them. For some it will be $10K for others it could be $50K but fewer with more skin in the game is important. 

Next I see so many founders drag out the process meeting just one more investor and just one more, after a certain time, just get it done, get it closed and move on. 

Just Closed: Time to Prep for the Next Round

So now we have closed the round, congrats. Now time to start prepping for the next round, one thing to remember, as a founder, you are always raising. So here is what we should do next:

  1. Sit down with our new lead investor and align on what we believe we need to hit to unlock the next round of funding. Will that next round come from them or external financing? 
  2. If external financing, what 5 names should we focus on?
  3. Make sure to send those 5 names monthly updates with your progress. Investors invest in lines not dots. 
  4. Make sure to meet them on a quarterly basis. 
  5. By the time of your next fundraise, following 6 face to face meetings and 18 updates, the investor and you will know if this is a partnership you want to pursue. 

I want your feedback. Did you enjoy this post? Let me know on Twitter here. 

Dec 19, 2022

Barry McCarthy is Peloton’s CEO and President. McCarthy is a seasoned executive who served as CFO of Spotify from 2015 to January 2020, and CFO of Netflix from 1999 to 2010. Prior to Netflix, McCarthy held various leadership positions in management consulting, investment banking, and media and entertainment. McCarthy has served on the boards of directors of Spotify and Instacart since January 2020 and January 2021, respectively. In addition, McCarthy has served as a member of the boards of Chegg, Eventbrite, MSD Acquisition Corp, Pandora, and Rent the Runway. 

In Today's Episode with Barry McCarthy We Discuss:

1. From Netflix to Spotify to Leading Peloton:

  • How did Barry make his way into the world of startups and come to work with Reed Hastings at Netflix? What are his single biggest takeaways from working with Reid?
  • Why did Barry decide to move to cold Stockholm to work with Daniel Ek and Spotify? What makes Daniel the special leader that he is?
  • Was Barry nervous about assuming the role of CEO @ Peloton? Are the elements he was most worried about the elements that are his biggest challenges today?

2. Barry McCarthy: The Leader

  • What does "high performance" in business mean to Barry?
  • Daniel Ek has described Barry as the "most strategic dealmaker in the world". What does Barry believe makes him so good at dealmaking? Where do so many go wrong?
  • Barry pioneered the model of the direct listing, why does he believe they are better? Why was it right as an approach for Spotify? Will we continue to see more?
  • What is Barry's framework for making tough decisions? How has it changed over time?

3. Barry McCarthy: The Master of Boards:

  • Barry has sat on some of the best boards from Netflix to Spotify to now Peloton and Instacart, what does Barry believe makes the best boards?
  • Where do many boards go wrong? Where do they become dysfunctional? What can and should be done to stop that?
  • How does Barry advise other board members on the right way to deliver tough news constructively?
  • What is the single biggest advice Barry would give to young board members assuming their first boards? Where do many young board members go wrong?

4. Barry McCarthy: Mastering the Mechanics:

  • Daniel Ek suggested that I had to ask about “demand creation theory and your ideas about whether the market is efficient”. What did he mean by this? How does Barry think about it?
  • How does Barry think about the interplay between gross margin, experience and retention?
  • Why did Barry decide it was the right decision to evolve the strategy from owning distribution to working with Amazon etc?

Dec 16, 2022

Hadi Partovi is a tech entrepreneur and investor, and CEO of the education nonprofit Before founding, Hadi founded two prior startups: Tellme Networks (acquired by Microsoft, discussed on 20VC with Emil Michael), and iLike (acquired by Newscorp). Hadi has also been an active advisor and angel investor to some of the best including FacebookDropboxairbnb, and Uber. If that was not enough, Hadi currently serves on the Board of Directors of Axon and MNTN.

In Today's Episode with Hadi Partovi:

1.) From the Iran-Iraq War to Founding Startups:

  • How Hadi and his family made their way from war-torn Tehran to the US and Silicon Valley?
  • How did seeing his family have nothing and struggle financially impact Hadi's mindset as an entrepreneur?
  • What does Hadi believe he is running from? What is he running toward?

2.) Lessons from Ballmer and Zuckerberg:

  • How did Hadi first come to meet a young Mark Zuckerberg when TheFacebook had less than 10 employees? Why did Hadi believe he was so special from that first meeting?
  • What are Hadi's biggest takeaways from working with Steve Ballmer? How did the reign and leadership of Ballmer compare to the reign of Bill Gates?
  • Hadi has helped both Facebook and Dropbox with their engineering hires, what is the secret to hiring amazing engineers? How does he structure the process? Where do so many go wrong?

3.) Hadi Partovi: The Leader:

  • How does Hadi define "high performance" in leadership? How has it changed with time?
  • What is Hadi's framework for making tough decisions? How does Hadi teach that framework to his team? What are the biggest mistakes leaders make in decision-making?
  • How important does Hadi believe speed of execution is? How does Hadi determine when is the right time to go slow to go fast?

4.) Hadi Partovi: The Person:

  • How does Hadi analyze his relationship with money today? How does it change over time?
  • Hadi stepped off the for-profit treadmill with, why did he make that decision? How does he avoid the trappings of chasing wealth?
  • How does Hadi think about ego and ego management today? How does Hadi separate self-worth from financial gain and accomplishment?

Items Mentioned in Today's Episode:

Hadi's Favourite Book: Sapiens: The #1 bestselling journey through human history and anthropology

Dec 14, 2022

Maggie Hott is the Director of Sales @ Webflow where she leads their Sales Dev, Account Executive, and Solution Engineering orgs. Prior to Webflow, Maggie spent an incredible 6 years at Slack in a period of hypergrowth for the company having joined as the founding AE scaling to a Sr Enterprise Leader. Before Slack, Maggie was the founding Sales hire at Eventbrite. If that was not enough, Maggie is also an active angel investor, an advisor to Cowboy Ventures, Scribble Ventures, and is a Founding Operator and LP @ Coalition Partners.

In Today's Episode with Maggie Hott We Discuss:

1. The Cold Email that Led to a World-Class Sales Career:

  • How a cold email to Kevin Hartz @ Eventbrite led to Maggie's career in sales?
  • What are the 1-2 biggest takeaways from her time at Slack? How did they impact her mindset?
  • What does Maggie know now that she wishes she had known when she entered sales?

2. The Sales Playbook: PLG and Enterprise:

  • How does Maggie define the sales playbook? What is it? What is it not?
  • Is it possible for early-stage companies to do both enterprise and PLG at the same time?
  • When is the right time to add enterprise to a PLG motion?
  • What are the steps to build an outbound sales engine in enterprise? Where do many go wrong?

3. Building the Bench: Hiring Your First Sales Team:

  • Should founders look to hire a Senior Head of Sales first or a more junior sales rep?
  • Should they be hired one at a time? What are the benefits of hiring many at the same time?
  • What is the right process to hire your first sales hire?
  • What are the core traits and habits that make the first 10x sales hire?
  • What are the right questions to ask to unveil those characteristics?

4. Making the Machine Work: The Process:

  • What can sales leaders do to proactively build relationships with other parts of the org?
  • How can more junior sales reps build relationships with other functions?
  • Why does Maggie believe that mis-hiring can be a $1M mistake? What are the early signs that a new hire is not working out in sales? How does this differ for outbound?
  • Why is it dangerous to make your self-serve product too good?

Dec 12, 2022

Ben Chestnut is the Co-Founder of Mailchimp, the all-in-one marketing platform for small businesses. Last year, in Sept 2021 it was announced that Intuit would acquire Mailchimp for a reported $12BN. There are so many things to love about the Mailchimp journey to this point. First, Mailchimp was founded as the result of a side project of a design agency Ben and his co-founder, Dan, used to run. Second, Mailchimp is and has always been based in Atalanta, eschewing the notion you have to be in SF or NYC to build a massive business. Then third, they never raised venture funding for the business all the way until their $12BN acquisition. Ben led Mailchimp to over 1,200 employees and millions of global users.

In Today's Episode with Ben Chestnut We Discuss:

1. From Mama's Kitchen to the Smell of Business and Founding Mailchimp:

  • How did Ben turn a mediocre agency into the founding of Mailchimp? What was the a-ha moment?
  • At what stage of the business did Ben quit the agency and go all in on Mailchimp? What sign did he need that Mailchimp had true product-market fit?
  • When Ben's mother died, he bought every flower in the local town to commemorate her. How did Ben's mother impact the type of father and husband he is today? How did she impact the way that he led Mailchimp as CEO?
  • Ben's fishing trips with his father played a big role in his early years, what were the single biggest lessons for Ben from his fishing trips with his father?

2. Ben Chestnut: The Leader:

  • How does Ben define the term "high performance" in leadership?
  • What does Ben mean when he says "the secret to happiness is to stay in your lane"?
  • Why would Ben describe himself as the "leader of the misfits"? How did that early experience and labeling impact both the people he hired and the culture he created at Mailchimp?
  • What does Ben mean when he says he used to have a "hands off, eyes off" leadership style? What have been the single biggest drivers in his development as a leader?

3. Ben Chestnut: The Person:

  • Relationship to Money: How does Ben reflect on his relationship to money? How has it changed over time? Why does Ben still to this day buy lottery tickets with his wife?
  • Conquering Fatherhood: What does being a great father to Ben mean? How does Ben attempt to instil the same work ethic and drive when his children are born into immense wealth?
  • The secret to Marriage: What does Ben believe is the core to a successful and thriving marriage? How does Ben view his role in the marriage? How has it changed over time?
  • Potential Lost Identity: A founder's identity is so closely tied to their company, how did Ben manage the challenge of selling his company but retaining his identity? What did Ben learn about himself through many different acquisition processes?

4. Mailchimp: The Business:

  • Why did Ben never raise venture money in the 21 year journey of Mailchimp?
  • Why did Ben never accept any of the acquisition offers that came before Intuit?
  • How did Ben motivate his team after they knew each acquisition offer was being turned down?
  • Why did Ben decide the acquisition by Intuit was the right decision for the company?
  • How does Ben view his role in the company now and moving forward?

Dec 9, 2022

Bob Pittman is Chairman and CEO of iHeartMedia, Inc., the number one audio company in America. Prior to iHeart, Bob has just had the most amazing career as a co-founder and programmer who led the team that created MTV. He has also led some of the most incredible turnarounds as CEO of MTV Networks, AOL Networks and Time Warner Enterprises and as COO of America Online, Inc. and later AOL Time Warner.

In Today's Episode with Bob Pittman We Discuss:

1. From Flying Lessons to Radio:

  • How Bob first made his way into radio at the age of 15?
  • What does Bob know now that he wishes he had known when he started his career?
  • What is the most painful lesson Bob has learned in his career that he is pleased to have learned?

2. Decision-Making in Leadership:

  • How does Bob structure all decision-making as CEO today?
  • Why does Bob ensure that all decisions are made within 24 hours? What are the pros and cons?
  • How does Bob prevent consensus decision-making? How does Bob create dissent in a discussion?
  • How do the best leaders know when to kill a project? What do most do instead?

3. Tactics vs Strategies: Why Plans Are BS!

  • What is the difference between a tactic and a strategy?
  • When is the right time to change your strategy and tactics?
  • What have been Bob's biggest lessons on how to get teams on board with tactical changes?
  • Why does Bob believe that plans are BS? When can they be useful?

4. The Secret to Messaging and Storytelling:

  • What does Bob believe is the universal truth to successful consumer messaging?
  • What has changed and what has not changed in the way companies tell stories to their customers?
  • Is there a difference between a great product and a great company? What are examples?
  • What excites Bob most about consumer habits today?

5. Bob Pittman: AMA:

  • What does Bob believe is the success to successful parenting? How has it changed?
  • How does Bob analyze his own relationship to money today? How has that changed?
  • Why does Bob not believe in legacy? What do people get most wrong when it comes to ego?

Dec 7, 2022

Marty Cagan is one of the OGs of Product and Product Management as the Founder of Silicon Valley Product Group. Before founding SVPG, Marty served as an executive responsible for defining and building products for some of the most successful companies in the world, including Hewlett-Packard, Netscape Communications, and eBay. He worked directly alongside Marc Andreesen and Ben Horowitz at Netscape and Pierre Omidyar at eBay.

In Today's Episode with Marty Cagan We Discuss:

1. Entry into the World of Product From Engineering:

  • How Marty first made his way into the world of product, having started life as an engineer?
  • What does Marty know now that he wishes he had known when he started in product?
  • What are Marty's biggest tips to anyone making the move from engineering to product?

2. Lessons from Marc and Ben at Netscape and Pierre @ eBay:

  • What are the single biggest lessons Marty took from working side by side on product with Ben Horowitz and Marc Andreesen?
  • What did Netscape do right? What did they do wrong? With hindsight, what would Marty have done differently?
  • How did Marty break all of his rules by working with Pierre Omidyar?

3. Hiring a World Class Early Product Team:

  • When is the right time to make your first product hire as a startup?
  • What is the right profile for that first product hire? Senior or junior?
  • If you go for the junior hire, how do you structure the rest of the team? If you go for the Senior hire, how do you structure the rest of the team?
  • What are the single biggest mistakes startups make when hiring their first in product?
  • Does Marty prefer someone with or without expertise in the domain you are in?

4. Mastering the Onboarding Process:

  • What is the optimal onboarding process for all new product hires?
  • How can leaders ensure that product hires see and understand all areas of the business?
  • What can product leaders do to proactively impress in the first 30-60 days?
  • What are clear red flags that a new product hire is not working out? How long do we give them?

Dec 5, 2022

Martin Casado is a General Partner @ a16z where he focuses on enterprise investing. At a16z, Martin has led investments and serves on the board of dbt Labs, Fivetran, Material Security, Ambient AI and many more incredible companies. Before venture, Martin was previously the Co-Founder and CTO at Nicira, acquired by VMware for $1.26 billion in 2012. While at VMware, Martin served as Senior VP and General Manager of the Networking and Security Business Unit, which he scaled to a $600 million revenue run-rate business.

In Today's Episode with Martin Casado We Discuss:

1. From $1.26BN Founder to Leading Enterprise Investing for a16z:

  • How did Martin make his way into the world of VC and come to lead enterprise investing for a16z?
  • What does Martin know now that he wishes he had known when he started investing?
  • What have been some of his biggest investing lessons from Marc and Ben?

2. The VC Model is Broken and Why:

  • Why does Martin believe that the current model for venture is broken?
  • Why does Martin believe that VCs are not oracles and they were not gifted with picking ability?
  • How will asset allocation more broadly fundamentally change over the next decade? Why will Silicon Valley take over and run Wall St?
  • Why does Wall St not care about innovation and true technological development?
  • Who will be the winners and who will be the losers in the next 10 years of venture?

3. Surviving a Crash - What Founders Need To Know:

  • Layoffs: What is Martin's advice to founders on doing layoffs today? How much is the right amount to cut? Should it be done in one go? How should this be communicated to investors and the board?
  • Scenario Planning: What three scenario plans should all founders be creating right now? How should they know which one is the right one to execute against?
  • Comparisons: How should founders use and look to public company performance and market cap to determine which plan they should choose?
  • Hiring Freeze: Why does Martin believe the biggest companies in the world make massive mistakes by freezing hiring? What should they do instead?

4. The Changing Guard at a16z:

  • What have been the single best and worst changes a16z have made over the last 24 months?
  • What are the first things to break when a firm scales as fast as a16z has done?
  • Does Martin agree a16z returns will reduce with the scaling of their funds larger than ever?
  • How does Martin look to train and educate his junior team? How does he advise them on surviving a downturn? What should they do? What should they not do?

5.) The Makings of a Great Board:

  • What are the three types of board members? What is the best? What is the worst?
  • What does Martin believe makes the truly great boards?
  • What is the biggest advice Martin gives to young board members today?
  • How has Martin changed as a board member over time? What does he need to improve?

Items Mentioned in Today's Episode:

Martin's Fave Book: The Weirdest People in the World: How the West Became Psychologically Peculiar and Particularly Prosperous

Dec 2, 2022

Will Hockey is the Co-Founder and Co-CEO @ Column, the only nationally chartered bank built to enable developers and builders to create new financial products. Before co-founding Column, Will was the Co-Founder, President, and CTO @ Plaid, a world-leading data network and payments platform. In 2020, Visa attempted to acquire Plaid for $5.3BN, however, this was blocked due to regulatory issues and the company went on to raise at a reported $13.4BN valuation just 9 months later. Additionally, Will is on the board of

In Today's Episode with Will Hockey We Discuss:

1.) The Founding of $13.4BN Plaid:

  • How did Will make his way into the world of startups and come to found Plaid with Zach?
  • If we are all a function of our histories, what is Will running from? What is he running toward?
  • What does Will know now that he wishes he had known when he started Plaid?

2.) Will Hockey: The Makings of a Decacorn Founder:

  • What does the term "high performance" mean to Will? How has this changed over time?
  • Having had such a successful time building Plaid to $13.4BN, how does Will assess his own relationship to risk and his relationship to money?
  • How does Will approach his own personal portfolio planning? Equity, debt, real-estate? How does Will optimize his own personal wealth?
  • Column is his second time founding a company, what did Will decide to take from Plaid that worked well? What did he decide he would not do having seen it work badly at Plaid?

3.) The Building of Truly Great Teams:

  • Why does Will believe that companies can be built so much slower than people think?
  • How does Will determine the decisions that have to be made fast vs those with time?
  • How does Will ensure the same size of urgency and speed within his team without this time or funding pressure?
  • What have been Will's single biggest lessons when it comes to people acquisition and retention?

4.) Fintech: The Next 10 Years:

  • How will the next 10 years look different from the last in fintech? What changes will be better? What will be worse? What is Will worried about? What is he excited about?
  • What does Will mean when he says, "the US financial system can function like a protocol"? What does Will believe are some of the core myths of the US financial system?
  • Why does Will believe the current financial system can and will fix a lot of what crypto is trying to solve? What barriers will prevent this from happening?

Items Mentioned in Today's Episode:

Will's Favourite Book: The World for Sale: Money, Power and the Traders Who Barter the Earth’s Resources, Merchants of Grain: The Power and Profits of the Five Giant Companies at the Center of the World's Food Supply

Nov 30, 2022

Jason Lemkin is one of the OGs of SaaS of the last decade. As the Founder of SaaStr, he has inspired more SaaS founders than one can imagine building "The World’s Largest Community for Business Software." Jason also invests out of the $100M SaaStr Fund and in the past Jason has led rounds into TalkDesk, Pipedrive, Algolia, Gorgias, Salesloft, and many more incredible companies. Prior to founding SaaStr, Jason was the Co-Founder of Echosign, an early e-signature business, funded by Emergence Capital and that was acquired by Adobe for $100M.

In Today's Episode with Jason Lemkin On Algolia We Discuss:

1.) Meeting the Unicorn: Algolia:

  • How did Jason first come to meet Nicolas (Founder) and Algolia?
  • What specific elements of cold emails make the best attract Jason's attention? What do they have in them? What are the most common mistakes people make with cold emails?
  • What is the single biggest mistake Jason made when making the deal with Algolia? How did Jason lead their seed round when their round was "oversubscribed"?

2.) Competition and TAM: The Reasons To Say No:

  • Competing with Free: How did Jason analyze the competitive landscape Algolia was facing? How did he gain comfort that they could compete and win against free and open-source?
  • TAM Analysis: The TAM at the time for Algolia was $2M. How did Jason analyze the TAM at the time? How did he get comfortable with such a small TAM?
  • What are the single biggest mistakes investors make when analyzing competition today? What are the biggest mistakes founders make when presenting the competitive landscape?
  • What are the single biggest mistakes investors make when analyzing TAM today? What are the biggest mistakes founders make when presenting the TAM and how it breaks down?

3.) Investing Lessons Transition from CEO to VC:

  • Jason has previously said one of his biggest lessons is "bet on what you know when you go from CEO to VC"? What did he mean by this?
  • How can one keep this operator knowledge and mentality when one is a VC for a long time?
  • What are the biggest pieces of advice that Jason would give to operators becoming investors?
  • What are the biggest mistakes that Jason made in his first 3 investments as a VC? How did he change?

4.) Mastering the World of Venture Today:

  • Why does Jason believe that he has become a worse investor with the rise of "remote investing"?
  • Why does Jason believe he is a worse investor without having a partner in SaaStr Fund?
  • Why does Jason believe that even the best founders do not want hard feedback anymore? Should we as VCs still give it to them? What has Jason learned here?
  • Will we see great LP churn and many LPs leaving the asset class? What will happen to the existing incumbents with massive AUM and reduced performance?

Nov 28, 2022

Miki Kuusi is the CEO of Wolt and Head of DoorDash International. In 2014 Miki founded Wolt with a mission to turn the smartphone into a remote controller for life, starting with delivering your favorite restaurant food, to you at home. Today Wolt operates in 23 countries, across several different categories, has over 4,000 employees, and last year, Doordash made the move to join forces with Wolt in a deal worth a reported $8.1BN. Previously, Miki was the CEO of Slush, one of the leading tech and investor events in the world attended by more than 25,000 people annually.

In Today's Discussion with Miki Kuusi:

1.) Founding Slush and Wolt: An Entry into Startups:

  • How did Miki come to found Wolt? What was that a-ha moment?
  • Did Wolt have product-market-fit from Day 1? What was the turning point when they did?
  • What does Miki know now that he wishes he had known when he started Wolt on Day 1?

2.) The Makings of a Truly Great Leader:

  • How does Miki define "high performance" today in leadership?
  • How does Miki think about what focus means in leadership? What is the hardest decision Miki has had to make when it comes to focusing the company? What did he learn from Ilkka @ Supercell?
  • What does Miki believe is the KPI of success as the CEO? How does it change?
  • What does Miki believe is the difference between good vs great leadership?
  • What does Miki believe is the biggest sacrifice he has made as the CEO?

3.) Hiring a Team to Compete on a Global Stage:

  • How does Miki use compensation to create a culture of ownership and accountability?
  • Does Miki start from a position of trust and it is there to be lost or no trust and it is there to be gained?
  • What is the difference between a team and a family in company building?
  • What is the core difference between trust and safety in company building? Why does Miki always want to have trust but not want to have safety?
  • What are the single biggest hiring mistakes that Miki has made? How has he learned from them?
  • Why does Miki believe you do not want to hire people that have done it before but hire the people who have seen those people do it before?
  • Why does Miki believe most companies are merely glorified recruiting operations?
  • Does Miki believe that companies need to be as big as they have grown into, headcount-wise?

4.) Miki Kuusi: The Personal Journey

  • What single day was the hardest day of the Wolt journey for Miki? How did it change him?
  • Why does Miki believe that for their Series B, all-bar one VC turned them down?
  • How does Miki assess his own relationship to risk and money today?
  • Why is Miki an advocate for founders taking secondaries along the journey?
  • What can Europe do to become a powerhouse in tech moving forward?
  • Why did Miki decide to sell the company to Doordash? What is he most excited to learn from Tony Xu, Doordash Founder and CEO?

Items Mentioned in Today's Episode:

Miki's Favourite Book: The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers

Nov 25, 2022

Casey Winters is the Chief Product Officer at Eventbrite. Prior to Eventbrite, Casey led the growth product team at Pinterest. Before Pinterest, Casey started the marketing team at Grubhub and scaled Grubhub’s demand-side acquisition and retention strategies. 

Elena Verna is the Interim Head of Growth at Amplitude. Former exec @ Miro, Netlify, SurveyMonkey. Growth Advisor to companies including Krisp, MongoDB, Ledgy, and SimilarWeb.

Kieran Flanagan is SVP Marketing at HubSpot, where he has helped the business grow internationally, move to a product-led business, quadrupled its marketing demand, and built out its media team, including the acquisition of ‘The Hustle.’

Andy Johns career started in growth at Facebook when the company scaled from 100M-500M active users. Since he has worked in some of the leading growth orgs at companies like Twitter, Quora and more recently at Wealthfront as Head of Growth and President.

Bangaly Kaba is the Director of Product Management @ Youtube. Prior to Youtube, Bangaly led the product growth and consumer product orgs at Instacart and before Instacart was Head of Growth @ Instagram, helping grow Instagram from 440M to > 1B monthly actives in 2.5yrs.

Ed Baker is a growth advisor to various startups including Lime, Zwift, Whoop, Crimson Education, GoPeer, and Playbook. Ed was the VP of Product and Growth at Uber from 2013-2017. Prior to Uber, Ed was the Head of International Growth at Facebook.

Adam Fishman was the Chief Product and Growth Offer @ Imperfect Foods. Before Imperfect, Adam was VP of Product and Growth @ Patreon, Before Patreon, Adam was the Head of Growth @ Lyft, Adam was the first growth and marketing employee hired and grew the team to 18 people.

In Today's Discussion on When To Hire a Head of Growth:

1.) When is the right time to hear your first growth hire?

2.) Is this hire a senior growth leader or a more junior growth engineer?

3.) What can early-stage startups do to entice senior growth leaders to their early-stage company?

4.) What data infrastructure should be in place prior to hiring your first growth hire?

5.) What does the optimal onboarding process look like for all growth hires?

6.) What can founders and CEOs do to set their growth hires up for success?

Nov 23, 2022

Jeffrey Katzenberg is an entertainment industry executive and entrepreneur, who throughout his career has repeatedly reshaped the media landscape. Jeffrey co-founded DreamWorks SKG, serving as CEO of DreamWorks Animation, which he grew into the world’s largest animation studio, known for ShrekKung Fu PandaMadagascar and more. In 2016, DreamWorks Animation was sold to Comcast for $3.8 billion. Before founding DreamWorks, Jeffrey was Chairman of The Walt Disney Studios, where he took the studio from last place to first at the box office with hits like Three Men and a Baby, Pretty WomanFather of the Bride and Sister Act. Most recently, Jeffrey co-founded WndrCo alongside Sujay Jaswa and has led WndrCo’s investments in Airtable,, Quibi, Vise,, NexHealth, Deel, and

Sujay Jaswa is one of Silicon Valley’s leading business innovators. At Dropbox, he created and led the company’s global business and finance organizations. Sujay and his teams raised over $1 billion, launched and scaled Dropbox’s products for businesses, created partnerships responsible for over 100 million users, executed some 20 acquisitions, and scaled the global business team from two to more than 500 employees in seven global offices. During this period, the company significantly scaled overall revenue from $12 million in 2010 to over $500 million run rate, Dropbox for Business revenue from $1 million to over $200mm run rate, and users from 15 million to 300 million. Most recently, Sujay Jaswa and Jeffrey Katzenberg co-founded WndrCo and Sujay has led WndrCo’s investments in Figma, 1Password, Databricks, Pango, Pilot, Rally, Zagat / The Infatuation, and other great companies.

In Today's Episode with Jeffrey Katzenberg and Sujay Jaswa:

1.) From Dreamworks and Dropbox to Venture with WndrCo:

  • How did Jeffrey and Sujay both make their way into the world of venture from Dropbox and Dreamworks?
  • What was Jeffrey's single biggest lesson from his time leading Dreamworks and being in Hollywood?
  • What was Sujay's biggest takeaway from being at the helm as COO at Dropbox?

2.) Operating Experience is Irrelevant and Can Be Dangerous:

  • Why does Sujay believe that operating experience is irrelevant?
  • What are the single biggest mistakes that operator investors make when it comes to advising their founders?
  • What do both Sujay and Jeffrey do to try and refresh their operating experience in real time?
  • How did Quibi impact their willingness and desire to take large risk both investing and operating?

3.) Building Teams and Hiring People:

  • What are the single biggest hiring mistakes Jeffrey and Sujay have made?
  • What did Jeffrey mean when he said at Disney, “if you do not come in on Saturday, do not bother coming in on Sunday”.
  • How do Jeffrey and Sujay feel about remote work? Why did it not work for them?
  • What did Alfred Lin @ Sequoia teach Sujay about the question all managers need to ask themselves on questing whether they should let someone go?

4.) Silicon Valley: Dead and Entitled?

  • Why does Jeffrey strongly disagree with the death of Silicon Valley?
  • What will happen to the generation of companies that raised too much with no product-market fit?
  • How will the mass layoffs in the valley change the valley as it is today?
  • Does Sujay agree that millennials are the worst segment to hire from? Are they entitled?


Nov 21, 2022

Semil Shah is the Founder of Haystack, one of the leading pre-seed and seed firms of the last decade. Among Semil's portfolio include the likes of DoorDash ($DASH), Instacart, Hashicorp ($HCP), Opendoor ($OPEN), Figma (acquired by Adobe), Carta and many more exceptional companies. Semil's first fund is marked between a 30 and 40x fund, astonishing.

In Today's Episode with Semil Shah We Discuss:

1.) The Makings of Semil Shah:

  • What is Semil running away from? What is he running towards?
  • What does Semil know now that he wishes he had known when entering venture?
  • What is Semil's biggest advice to managers raising their first funds now?

2.) Fund Sizing: Growing vs Staying Disciplined:

  • Question from Hunter Walk: How does Semil determine the right size fund to raise with each fund
  • Question from Satya Patel: Why have you resisted increasing AUM?
  • In the last episode Semil mentioned a three-year deployment cycle for the fund, did he stick to it? What are the benefits and drawbacks?
  • What investing mistakes did Semil make over the last 3 years that he wishes he had not made?  

3.) The Secret to Fundraising for a Fund:

  • What is Semil's biggest advice to emerging managers on finding new LPs? What works?
  • What materials do managers need to have in place for a new fundraise? Deck? Dataroom?
  • What are the most common mistakes VCs make when pitching LPs their funds?
  • How does Semil follow-up with potential LPs post-call? What works? What does not?
  • How does Semil suggest creating a sense of urgency for LPs to commit to a fund?
  • How does Semil feel about giving preferential terms to convince LPs to commit to the first close?

4.) The Current Landscape:

For VCs:

  • How will the current landscape impact emerging managers' ability to raise?
  • What advice would Semil give to them? Raise smaller?
  • Kyle Harrison said on the show recently, “differentiation will kill 80% of venture firms, especially the so-so ones”. Does Semil agree? Who is set to struggle? Who is set to thrive in this environment?

For LPs:

  • What does Semil think are the biggest mistakes LPs made over the last 2-3 years?
  • How will they respond in this market cycle?
  • If Semil were handed an endowment fund, how would he allocate today?
  • Does Semil agree, we will see a denigration of venture returns to those of PE like multiples? Why?

For Founders:

  • How does Semil advise founders on raising today when everyone says they are investing but very few really are?
  • How does Semil advise founders on how to think about valuation inflection points with respect to raising capital?

Items Mentioned in Today's Episode:

Semil's Favourite Article: Master of Play

Semil's Most Recent Investment: Impart Security

Nov 18, 2022

Oana Olteanu is a Partner @ SignalFire where she focuses on enterprise software at Seed, Series A and Series B. Prior to joining SignalFire, Oana was at Scale Venture Partners where she invested in applied ML and developer tooling. Oana sourced Scale’s investments in, Flatfile, and Proscia. She was part of the deal teams for Honeycomb and AllyO (acquired by HireVue). She also supported existing portfolio companies such as Dialpad, Matillion, and BigID. Prior to Scale, Oana was an AI seed investor at, SAP’s $35M seed fund, where she sourced the investments in, and Akorda.

In Today's Episode with Oana Olteanu We Discuss:

1.) From Tank Driving in Romania to VC's Rising Star:

  • How Oana made her way from driving tanks in Romania to becoming a VC?
  • How did leaving Romania for Germany and then moving to the West Coast impact her mindset?
  • What does Oana know now that she wishes she had known when she entered VC?

2.) How to Assess a VC: The Founders Guide:

  • Pre-investment, how can founders know whether a VC can add value? What are the signs?
  • What three core questions will reveal how much value a VC can add?
  • Post-investment, what can founders do to extract the most value from their VCs?
  • What should the founders ask their investors for help with? What should they do themselves?

3.) The VC <> Founder Relationship:

  • Oana has the highest founder NPS of any VC I have ever had on 20VC, what does Oana believe makes her founders rate her contribution so highly? What works? What does not?
  • How does Oana give sometimes very hard feedback to founders but retain that relationship of trust and safety at the same time? What mistakes do other VCs make in giving feedback?
  • What does Oana believe are the single biggest misalignment between VCs and founders?

4.) VCs Behaving Badly: 101

  • What are the single biggest ways Oana sees VCs behaving badly?
  • How does Oana think founders expectations of the product of venture should change?
  • Does Oana believe boards are valuable? What can be done to improve them?

Items Mentioned in Today's Episode:

Oana's Favourite Book: The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living: Featuring new translations of Seneca, Epictetus, and Marcus Aurelius

Nov 16, 2022

Oliver Jay (OJ) is one of the most successful sales leaders of the last decade. Most recently, OJ spent 6 years as CRO @ Asana and grew the team from 20 to over 450, becoming a master in sales onboarding in the process. Before Asana, OJ spent 4 years at Dropbox, where OJ was Head of APAC & LATAM.

Jordan Van Horn is a Revenue Leader @ Monte Carlo. Prior to this role, Jordan spent 4 years at Segment as VP of Sales, leading a sales team of 50+ Account Executives. Before Segment, Jordan was at Dropbox for 4 years leading enterprise sales for Dropbox Business.

Dannie Herzberg is a Partner @ Sequoia Capital and before Sequoia, Dannie spent 4 years at Slack as their Head of Enterprise Sales, growing the business from $100M – $1B in revenue. Before Slack, Dannie spent over 5 years at Hubspot building sales teams.

Zhenya Loginov is the CRO @ Miro. At Miro, Zhenya runs the go-to-market team of 700+ people across. Prior to Miro, Zhenya was the COO @ Segment where he built and ran the global go-to-market team of 200+ people. Pre-Segment, Zhenya led a 100-person team at Dropbox across different functional areas.

Lauren Schwartz is VP of Enterprise Sales at Fivetran, where she has scaled the team to nearly 100, while more than tripling enterprise revenues. Previously, Lauren spent close to 4 years at Segment where she started as the first female AE and ultimately built and led sales teams in enterprise and growth.

Kyle Parrish is VP Sales @ Figma, where he built the sales engine from scratch to today, with over 100 in sales. Before Figma, Kyle spent over 5 years at Dropbox in numerous different roles including Head of Sales, and Global Partnerships lead, responsible for growing Dropbox’s partner ecosystem.

In Todays Episode on Sales Onboarding We Discuss:

1.) How should the onboarding process for all new sales reps be structured?

2.) How should the onboarding process for a new sales leader be structured?

3.) What specific things can leaders do to set both reps and leaders best up for success?

4.) What are the single biggest red flags in the first 30 days that a rep is not going to work out?

5.) What tools and software can be used to improve this process of ramping new reps?

Nov 14, 2022

Cathie Wood is the CEO & CIO @ ARK Invest, focusing solely on disruptive innovation, primarily in the public equity markets. ARK has become renowned for opening up its research and becoming a ‘sharing economy’ company in the asset management space. Prior to ARK, Cathie spent twelve years at AllianceBernstein as CIO of Global Thematic Strategies where she managed over $5 billion. Cathie joined Alliance Capital from Tupelo Capital Management, a hedge fund she co-founded, which managed $800 million in global thematic strategies. Prior to Tupelo Capital, she worked for 18 years with Jennison Associates LLC as Chief Economist, Portfolio Manager and Director. 

In Today's Episode with Cathie Wood We Discuss:

1.) Entry into Hedge Funds at 20:

  • How did Cathie get her first role in the world of finance at the tender age of 20?
  • What is Cathie running from? What is Cathie running towards?
  • What are some of Cathie's biggest lessons from seeing the dot com bust at Tupelo?
  • What does Cathie know now that she wishes she had known when she started investing?

2.) Why Benchmarks and Passive Investing are Bad:

  • Why does Cathie believe that benchmarks and indexes have become dangerous for consumers?
  • Why does Cathie not believe what everyone else does regarding inflation?
  • How much of the performance of large-cap tech stocks is tied to the growth of passive investing?
  • Why does Cathie think the Fed is making a huge mistake?

3.) Time to Pick Companies:

  • Why does Cathie believe that Facebook is emerging as an attractive value stock?
  • How does Cathie believe Elon Musk and Jack Dorsey could build the largest universal wallet?
  • If Cathie were to put all her money into one of their companies, what would it be?
  • Why does Cathie believe Zoom is one of the most misunderstood companies?

4.) Why Venture: Why Now:

  • Why did Cathie decide to do a venture fund with ARK now?
  • Why did Cathie decide to do a no-carry structure with a higher management fee? How does that align incentives with investors?
  • In venture, the asset chooses the capital, how does Cathie analyze why the best founders in the world will pick and work with ARK over other amazing VCs?
  • What is the single biggest risk you are underwriting when investing in ARK's venture fund?

Items Mentioned in Today's Episode:

Cathie's Favourite Book: The Emperor of All Maladies: A Biography of Cancer

Nov 11, 2022

Martín Escobari is Co-President, Managing Director and Head of General Atlantic’s business in Latin America. Martín is Chairman of the firm’s Investment Committee and also serves on the Management and Portfolio Committees. Before joining General Atlantic in 2012, Martín was a Managing Director at Advent International. Prior to that, he was Co-Founder and CFO of, a leading Brazilian online retailer that went public and was sold to Lojas Americanas in 2006. Martin started his career as a management consultant at The Boston Consulting Group. Thanks to Seba Kanovich @ dlocal for the introduction today.

In Today's Episode with Martín Escobari:

1.) From Bolivia to Harvard to Leading General Atlantic:

  • How did Martin make his way into the world of venture from a small town in Bolivia?
  • How did being an operator going through a bust impact how Martin invests and works with founders?
  • How does Martin advise young members on his team about surviving through a bust?

2.) Market Matters: Founders, Product or Market:

  • Why does Martin believe the single most important element when investing is the market you are entering?
  • How does Martin assess both market size and market growth?
  • What does Martin believe makes a "beautiful business model"? What is the difference between good vs great? Why have we seen a generation of bad business models?
  • How did Martin's analysis of Nubank's market lead him to turn them down? How did Martin change his approach to investing on the back of turning down Nubank?

3.) The Venture Landscape:

  • What made Martin believe there was a downturn last year? What three signs always suggest we are in a bubble?
  • As a result, how did General Atlantic retain their discipline when others did not? Where did they lose their discipline and invest at the top of the market?
  • How does Martin analyse the performance of the crossover funds in the last 24 months? Who did well? Who did not? Do they remain in the market?
  • Is Martin concerned by the exodus of capital out of South America with the bust?

4.) Martin Escobari: The Investor and Board Member:

  • How has Martin's style of investing changed over the last decade?
  • How does Martin reflect on his own price sensitivity? Does Martin engage in outcome scenario planning?
  • What has been Martin's biggest hit? How did it change his mindset?
  • How would Martin analyze his own style of board membership? How does Martin advise young board members gaining their first boards?

Nov 9, 2022

Hugo Barra is the OG of consumer hardware of the last decade. In Hugo's current position, he is the CEO @ Detect, building tools that empower people to understand their health and make informed, timely decisions. Before Detect, Hugo spent an incredible 4 years as VP of VR @ Meta with Oculus. Prior to Oculus, Hugo was in China as VP of Global @ Xiaomi, the 3rd largest phone maker in the world. Finally before Xiaomi, Hugo was a product leader @ Google for over 5 years including as VP of Android Product Management.

In Today's Episode with Hugo Barra We Discuss:

1.) Entry into Product:

  • How did Hugo make his way from Brazil to Silicon Valley and Beijing Product OG?
  • What is one takeaway from Google, Meta, and Xiaomi that influenced the way Hugo approaches product today?
  • What is 996 Chinese work culture? How does the experience of working and leading teams in China impact his approach to team building today?

2.) The Secret to Success in Hardware:

  • Why is hardware so much harder than software? What are the main differences?
  • What are the biggest challenges faced when building V1 and V2 in hardware? How much do you rely on data vs gut and intuition?
  • What are some of Hugo's biggest consumer product hardware failures? What did he learn from them?

3.) Feature King vs Budget King:

  • Previously Hugo has said, "in the beginning, there is only two types of consumers." What does he mean by this? How does that impact his approach to product building?
  • Can a budget king product leader also be an amazing feature king leader? What is the difference in the two? Why is it harder to be a budget king product leader?
  • What happens if you have both budget king and feature king in one product? What happens then?

4.) Product Management 101:

  • How does Hugo define product management today? What does it really mean to Hugo?
  • Gustav @ Spotify has said before, "details are not details, they are the product." How does Hugo think about this statement in terms of great product management today?
  • When do product orgs start to break down? What are the catalysts? What can be done to stop this?

5.) Brand Marketing vs Product Marketing:

  • What is the difference between product and brand marketing?
  • Why does Hugo believe you should always start every product build with the press release? What is the difference between good and great in a press release? What do the best have?
  • What are the single biggest mistakes founders and product leaders make in storytelling today?

6.) Masterclass in Hiring:

  • Why does Hugo do 3-and-a-half-hour interviews when hiring new candidates?
  • What are the benefits of their being so long? What does he want to achieve?
  • What core questions does he ask every time? What differentiates good from great?
  • How does he get people to really open up and show true vulnerability?

Nov 7, 2022

Brian Armstrong is the Co-Founder and CEO @ Coinbase, the easiest place to buy and sell cryptocurrency. Over the last 10 years, Brian has led Coinbase to today, a public company with over 3,500 employees and revenues of over $7.5BN in 2021. Brian also raised venture funding before going public from some of the best including Fred Wilson @ USV, Micky Malka @ Ribbit, Marc Andreesen @ a16z and Garry and Alexis at Initialized. Prior to founding Coinbase, Brian was a Product Manager @ Airbnb.

In Today's Episode with Brian Armstrong We Discuss:

1.) Founding Coinbase:

  • How did Brian make his way from PM @ Airbnb to founding Coinbase?
  • What is Brian running from in his past? What is he running toward in his future?
  • What does Brian know now that he wishes he had known at the start of Coinbase?

2.) Brian Armstrong: The Leader:

  • What does "high performance" mean to Brian in leadership?
  • How does Brian think about stepping off the treadmill for a second and appreciating what has been achieved? How does one celebrate as a team without creating laziness or arrogance?
  • How has Brian most changed as a leader over the last 10 years?
  • On reflection, what does Brian believe are his biggest weaknesses today?

3.) Crucible Moments in the Coinbase Journey:

  • What does Brian mean when he says, "you need to be able to differentiate between a real emergency and a fame emergency?" What is the difference?
  • When Brian made the speech to the Coinbase team on political views in the company, was that a real or fake emergency? What happened? What would he have done differently?
  • Is the failed NFT launch, a real or fake emergency? What big mistakes were made? What are Coinbase doing to correct and improve them?
  • "Bankrupt Coinbase" campaign on social earlier this year, real or fake emergency? What has been Brian's biggest lessons on how to deal with fake news?

4.) Crypto and The Ultimate Mission for Coinbase:

  • What is different about this crypto winter from all other crypto winters?
  • Why did Brian ban discussion on the market cap from employees within Coinbase?
  • How does Brian maintain morale internally when everyone sees the stock at all-time lows?
  • How does the Coinbase mission extend far beyond financial freedom for the world? What does Brian want Coinbase to be in 10 years?


Nov 4, 2022

Michael Mauboussin is Head of Consilient Research at Counterpoint Global. Previously, he was Director of Research at BlueMountain Capital, Head of Global Financial Strategies at Credit Suisse, and Chief Investment Strategist at Legg Mason Capital Management. He is also the author of three incredible books, including More Than You Know: Finding Financial Wisdom in Unconventional Places, named in The 100 Best Business Books of All Time by 800-CEO-Read. Michael has taught at Columbia Business School since 1993 and received the Dean's Award for Teaching Excellence in 2009 and 2016.

In Today's Episode with Michael Mauboussin We Discuss:

1.) Entry into Venture and Finance:

  • What does Michael actually do as "Head of Consilient Research"?
  • What does Michael know now that he wishes he had known when he entered finance?
  • How did Michael and Bill Gurley meet in business school? What does Michael believe makes Bill such a special investor today?

2.) Booms and Busts: How This Compares?

  • How does the current macro downturn compare to prior crashes Michael has worked through?
  • What is the same? What is different? How do political and health events impact the macro?
  • Why was 1987 the end of the world at the time? How did the recovery take place?
  • How does Michael analyze the duration of bull markets vs the duration of recovery time?
  • What advice does Michael give to young people today questioning if they are good investors?

3.) The Investment Decision-Making Process:

  • How does Michael advise on the structuring of your decision-making process?
  • What makes a good process vs a bad process?
  • What can be done to remove politics from the decision-making process?
  • What can be done to ensure all people, regardless of hierarchy feel safe in the process and feel they can share their thoughts without repercussions?
  • What are the single biggest mistakes Michael sees people make in their decision-making process?
  • How do you know when is the right time to change your process?

4.) Everything is a DCF:

  • What does Michael mean when he says that "everything is a DCF"?
  • How does Michael advise and apply this thinking to early-stage venture investors?
  • How does Michael think through highly diversified portfolios vs super concentrated portfolios in venture?

Items Mentioned in Today's Episode:

Michael's Favourite Book: Consilience: The Unity of Knowledge by E.O Wilson

Nov 2, 2022

Raf Illishayev is the Co-Founder and CEO @ GoPuff, one of the market leaders delivering daily essentials in minutes. GoPuff’s latest funding round priced the company at a reported $8.9Bn in March 2021 and to date, Rafael has raised over $2.4Bn for the company from the likes of Accel, Softbank, Fidelity, Baillie Gifford, D1 Capital and more. Rafael has scaled the company to over 1/3 of the US with over 12,000 employees nationwide.

In Today’s Episode with GoPuff's Rafael Ilishayev You Will Learn:

1.) From Student to Global CEO:

  • How Raf came up with the idea for GoPuff and started the company as a student with no funding?
  • What were the early signs of product-market fit that Raf observed in the early days?
  • In hindsight, does Raf wish they had raised external funding sooner than they did? What would raising external funding sooner have changed about the way they run the business?

2.) The Rise and Fall of Quick Commerce:

  • What are the core drivers that have led to capital drying up for players in the quick commerce space?
  • With the changing environment, is it a race to profitability for all providers in the space?
  • Is this the perfect time for GoPuff to acquire? What are the characteristics of businesses in the space that GoPuff would vs would not like to acquire?
  • How does Raf see the quick commerce space looking in 5 years time?

3.) Getting to Profitability: The Levers That Matter:

  • Customer Service: Why does Raf believe that all players pulling back on investing in customer service are making a massive mistake? What can be done instead?
  • Delivery Time: Why does Raf believe the 10-minute delivery model is fundamentally unprofitable? How do GoPuff approach it as a result?
  • Inventory: With a changing macro-environment, why does Raf believe it is prudent to focus more attention on alcohol and convenience goods? What do prior recessions show us about consumer spending patterns changing?
  • Metrics: What are the single most important metrics which dictate the speed of getting to profitability? Why is the amount of orders a driver can deliver per hour the most important metric?

4.) Business Expansion Opportunities:

  • How does Raf analyze the opportunity for GoPuff in Europe?
  • Why does Raf believe they should have pulled out of Spain much sooner? Why are they so focused on the UK now?
  • Why does Raf believe it is the right decision to stop investing in GoPuff pharmacy?
  • Why is Raf so bullish on GoPuff kitchens? How does the unit economics of the kitchens compare to the core business for GoPuff? What are the positive effects of kitchens on GoPuff core product?
  • What was the most recent disagreement the board has had when it comes to determining what to prioritize vs what not to?

Mentioned in Today's GoPuff Episode:

Raf's Mentor and Advisor: Emil Michael, Former Chief Business Officer @ Uber

Oct 31, 2022

Brian Singerman is a Partner @ Founders Fund, one of the best-performing funds of the last two decades. Among their portfolio, they have the likes of Airbnb, Facebook, Stripe, Anduril, and many more generational-defining companies. As for Brian, he has led investments in the likes of Affirm, Oscar Health, Wish, Asana, Oculus, and Postmates to name a few. Brian also sits on the board or is an observer to The Long Term Stock Exchange, Solugen, Cloud9, Modern Health, and of course, Anduril. Prior to Founders Fund, Brian spent a very successful 4 years as an engineer and executive at Google.

In Today's Episode with Brian Singerman We Discuss:

1.) From Google to Befriending Sean Parker to Founders Fund:

  • How Brian's friendship with Sean Parker led to his joining Founders Fund over 15 years ago?
  • What does Brian believe makes Founders Fund such a unique fund?
  • What does Brian know now that he wishes he had known when he started in venture?

2.) The Landscape Today: Where Are We Now?

  • Why does Brian believe there is a huge price mismatch between private vs public companies?
  • How does this impact the pace with which Founders Fund invest? Why does Brian not feel any pressure to invest in this environment?
  • What are the 10 hypergrowth companies that Brian is looking to invest in today?
  • What advice does Brian give to young investors today who are concerned at their first market correction and questioning if they are actually any good at this?

3.) Brian Singerman: The Investor:

  • How does Brian reflect on his own investing style? What is he world-class at? What is he bad at?
  • Why does Brian think boards are a waste of time? What is better than a board?
  • Why does Brian not ever think about reserves? How does Brian answer LPs concerns when they cite them on the topic of cross-fund investing?
  • What does Brian believe is the secret to venture capital? What elements make those at Founders Fund thrive? What characteristics make those that do not work out, fail?

4.) Founders Fund: The Firm:

  • How does Founders Fund structure and optimize its decision-making process today?
  • How does Founders Fund approach the hiring process for all new team members? What one question do they need to be able to clearly answer with all team members joining?
  • How do Founders Fund approach the reference checking process for all new hires? What questions do they find most revealing of the true talent of the candidate?
  • What are the single biggest hiring mistakes Brian has made? What did he learn from them?

Items Mentioned in Today's Episode:

Brian's Most Recent Investment: Anduril

Oct 28, 2022

Chris Sacca is the Founder and Chairman @ Lowercase Capital, one of the best performing funds in the history of venture capital with a portfolio including Uber, Stripe, Twitter, Instagram, Twilio, Docker and many more.

  • From interviewing some of the world's richest married couples, how did gaining wealth change their relationship and marriage?
  • What does Chris do to actively ensure his children remain hungry and know the value of money?

Chamath Palihapitiya is Founder & CEO @ Social Capital. Social’s portfolio includes the likes of Slack, Yammer, Front, Intercom and Carta to name a few.

  • What does Chamath mean when he says we need to think through the mindset of "infinite games" not finite games? How does this change how you think about money?
  • How does Chamath think about his relationship to risk today as a result?

Brad Gerstner is the Founder and CEO of Altimeter. Brad’s notable deals that he has helped lead include Snowflake, Mongo, Bytedance, Gusto, Unity, Okta, dbt, Modern Treasury, EPIC Games, Hotel Tonight and Zillow.

  • What is the most important thing parents can do to ensure that despite wealth, their children remain grounded and ambitious?
  • Why does Brad, despite being a billionaire, still live in a modest house and not spend on the excesses of life? How does Brad embrace essentialism with wealth?

Cyan Banister is one of the most successful and renowned early-stage investors in the last decade. Her portfolio includes the likes of SpaceX, Uber, Affirm, Opendoor Postmates, Niantic and Thumbtack to name a few.

  • Why did Cyan used to hate money? Why was she "anti-capitalist"?
  • How does Cyan approach risk management today? Why does she invest every dollar she makes back into the ecosystem?

George Zachary is a General Partner @ CRV, one of the nation's oldest and most successful early-stage venture capital firms with a portfolio including the likes of Airtable, DoorDash, Dropbox, Niantic and many more.

  • What did George learn about how the way people view you changes with your increasing wealth?
  • Why does George believe rich people like to hang out with rich people?

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.

  • What does Biz mean when he says, "wealth only serves to amplify the person you are?"

Oct 26, 2022

Vaibhav Sahgal is VP of Consumer Product @ Reddit where he has been for close to 5 years. Prior to his leading consumer product, Vaibhav spent 3 years as Head of Growth at Reddit. Before Reddit, Vaibhav spent an incredible 8 years at Zynga across different roles including Director of Product and GM for "Words with Friends".

In Today's Episode with Vaibhav Sahgal We Discuss:

1.) Entry into Product + Growth:

  • How did Vaibhav come to lead some of the best growth orgs in the world at both Reddit and Zynga?
  • What are 1-2 of Vaibhav's biggest takeaways from working with Mark Pincus @ Zynga?
  • What is the most painful growth lesson that Vaibhav learned that he is also pleased to have learned?

2.) WTF Really is "Growth":

  • How does Vaibhav define growth today? What is it not?
  • How does Vaibhav fundamentally differentiate between value connection and value creation?
  • Is growth an art or a science? What tactics have died a death? What remains stronger than ever?

3.) Hiring Your Growth Team:

  • How does Vaibhav advise founders on when is the right time to hire their first growth professionals?
  • Where should they sit within the org? In product? In marketing? Standalone growth team?
  • What are the biggest mistakes Vaibhav sees founders make when hiring their first growth hires?

4.) The Interview Process:

  • How does Vaibhav structure the interview process for all new growth hires? What are the steps?
  • What are the must-ask questions when hiring for growth? What are good answers?
  • How can founders use case studies and data to determine the quality of a growth candidate?

5.) The Onboarding and Integration:

  • What is the optimal onboarding process for all new growth hires?
  • What are signs in the first 3 days that a growth hire will vs will not work out?
  • What can leaders do to ensure growth hires are integrated with the rest of the teams?
  • What are the biggest mistakes founders make when onboarding growth hires?

Items Mentioned in Today's Episode:

Vaibhav's Favourite Book: Andrew Chen: The Cold Start Problem

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