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