Shishir Mehrotra is the Founder & CEO @ Coda, the startup that brings all of your words and data into a flexible all-in-one doc. To date, Shishir has raised over $140M from some great names including Greylock, Kleiner Perkins, General Catalyst, NEA and Homebrew to name a few. Prior to founding Coda, Shishir spent an incredible 6 years at Google in a couple of different roles; first as Director of Product for Youtube Monetisation and then moving to Youtube VP of Engineering, Product and UX. Before Google, Shishir was with Microsoft for 6 years as a Director of Program Management. Shishir also serves on the board of Spotify.
In Today’s Episode You Will Learn:
1.) How Shishir made his way into the world of tech, came to be VP of Engineering, Product and UX @ Youtube and how it led to founding Coda?
2.) What is the No 1 quality of a good decision? How does Shishir think through reversible vs irreversible decisions? What are the 4 phases of decision-making? When should decisions be based on speed vs not? How can teams adjust questions to come to more productive outcomes?
3.) How does Shishir encourage debate and dissent within team discussions? How can leaders build deep trust with their teams? How can leaders create true democracy for idea sharing and meritocracy? Should ideas always be acted on immediately? What are the pros and cons?
4.) How does Shishir think about and evaluate his own operating cadence? How has this changed over time? How does Shishir approach time allocation? What have been his core learnings? How does Shishir divide his time between proactive and reactive tasks?
5.) How does Shishir approach OKR setting? What can leaders do to create aspirational and inspirational goals? How should goals be correctly communicated across orgs? How many OKRs should one team/person have? How should attribution across OKRs be given?
Items Mentioned In Today’s Show:
Shishir’s Fave Book: Switch: How to change things when change is hard
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Alex Pall and Drew Taggart are the Founders of The Chainsmokers and Mantis. The Chainsmokers are one of the most sought after musical acts of our time. As for Mantis, just last week they announced their first $35M venture fund and have backing from Ron Conway, Mark Cuban and Keith Rabois. They have already invested in hotly contested rounds for Fiton and Loansnap. Drew and Alex also own a production studio, are stakeholders in the spirit brand JaJa Tequila and last year co-founded the anti-scalper ticketing platform Yellowheart.
In Today’s Episode You Will Learn:
1.) How Drew and Alex made their way into the world of tech and startups and how they came to found a venture firm with Mantis?
2.) Why did Alex and Drew decide now was the right time for the fund? What did they look for in their LPs? How do they use their LPs to strategically help their companies? What is their preferred stage, sector? Do they have ownership requirements?
3.) Are Alex and Drew nervous about making the move into venture? If everyone has a chip on their shoulder, where does the chip on their shoulder come from? How do they think about their own vulnerabilities? How do they manage them? What works? What does not?
4.) What ways do Alex and Drew most like to work with their founders? Where do they provide outsized value? What are some examples of this? How do they think about working with VCs to get into the best rounds? How do they want to position Mantis in the ecosystem?
5.) With the tequila brand, the film production company and now the venture fund, how do they think about the expansion of "The Chainsmokers Empire"? What does this look like in 10 years? How would they like it to expand and grow?
Items Mentioned In Todays Episode
Drew's Favourite Book: The Unbearable Lightness of Being
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Austen Allred is the Founder & CEO @ Lambda School, the startup that remotely trains people to become a web developer or data scientist and the students pay no tuition until they are hired. Just last month, Lambda's $74M Series C was announced led by Gigafund bringing their total funding to date to over $129M with prior investors including Stripe, Bedrock, GV, Gigafund and GGV to name a few. Prior to founding Lambda, Austen was Senior Manager for Growth @ LendUp and before that co-founded Grasswire.
In Today’s Episode You Will Learn:
1.) How Austen made his way into startups having slept in a Honda Civic and how he went from homeless to rockstar founder @ Lambda?
2.) How does Austen evaluate his own attitude to risk? How does Austen think about downside protection today? How has this changed over time? How does Austen feel about founders taking secondaries? How does Austen think about his own relationship to money?
3.) Having raised his Series C last month, why did Austen choose the investors he did? How did the round progress? What made Gigafund different to alternate options? What makes the best board members in Austen's mind? What makes the worst?
4.) What have been the most challenging elements for Austen of scaling the team? How does complexity change with time in team scaling? Why did Austen bring in a COO? What did he look for in the role? How does Austen advise others on bringing in a COO?
5.) Why does Austen believe that post-COVID we will never go back to the valley as we knew it? Why does Austen believe the valley represents the biggest potential squandering of wealth in history? How does Austen evaluate the government intervention we have seen?
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Ravi Gupta is a Partner @ Sequoia Capital, one of the world's leading venture firms with a portfolio including the likes of Airbnb, Instacart, Stripe, UiPath, Zoom, the list goes on. As for Ravi, prior to Sequoia, he spent 4 years as COO & CFO @ Instacart playing an integral role in their hyper-growth journey. Before that Ravi spent 10 years as a Director @ KKR.
In Today’s Episode You Will Learn:
1.) How Ravi made his way from KKR to being one of the key execs leading Instacart? How Instacart led to Ravi becoming a Partner @ Sequoia?
2.) When thinking about team, what does Ravi believe is the single most important question to ask? How does Ravi determine between good and great when assessing talent? What are the leading indicators? What have been Ravi's lessons on what it takes to acquire those great talents?
3.) How does Ravi think about and approach prioritisation today? How does Ravi analyse what to delegate vs what to control? Should you get good at your weaknesses and double down on strengths? How does Ravi think about vulnerability within leadership? How did he show that vulnerability as a leader at Instacart?
4.) In joining Sequoia, what has Ravi been most impressed with in regards to the team? What has he been most surprised by? Why is Ravi so bullish unanimous decision-making is right? How do founders determine which Sequoia Partner will be on their board?
5.) How does Ravi think about what it takes to be the very best board member? Who is the best board member Ravi has worked with? What made them so special? What advice does Ravi give to new board members adopting board seats for the first time?
Items Mentioned In Today’s Show:
Ravi’s Fave Book: Clay Christensen: How Will You Measure Your Life?
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Alex Tew is the Co-Founder and Co-CEO @ Calm, the #1 App for Meditation and Sleep allowing you to find your calm, sleep more, stress less and live better. To date, the company has raised over $143M in funding from some of the best including Lightspeed, Insight, TPG and then some very cool names such as Ashton Kutcher, Harry Styles, Brad Feld and Jason Calacanis. Prior to Calm Alex founded numerous other startups including PopJam, Pixelotto and most famously rose to internet fame with his founding of The Million Dollar Homepage.
In Today’s Episode You Will Learn:
1.) How Alex went from playing Fifa with Michael Acton Smith in Berwick St, London to founding one of the hottest startups in the valley, Calm?
2.) What does Alex believe the very best brands do today? How do they message? How do they present? How do they divide opinion? How did Alex think about the early Calm brand? How has it changed? How does Alex advise others looking to build a company brand?
3.) Does Alex agree with Peter Fenton, "there is a lack of free and open distribution"? How does Alex analyse the economics for customer acquisition costs today? What is a good paid vs organic ratio? How do CACS change over time in Alex's experience?
4.) What have been Alex's biggest learnings on what it takes to build a viral product? Where do many people go wrong? Why does Alex believe pressure is the enemy of creativity? Does Alex believe people should create time for creative thought? What does Alex do to stimulate idea creation?
5.) How has Alex seen himself evolve and develop as a leader over the last 5 years? What have been the hardest elements to scale? How does Alex think about effective delegation? What have been Alex's biggest lessons on what it takes to hire A* people consistently?
Items Mentioned In Today’s Show:
Alex’s Fave Book: Godel, Escher, Bach: An Eternal Golden Braid
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Angela Strange is a general partner at Andreessen Horowitz, one of the leading venture firms of the last decade with a portfolio including the likes of Facebook, Github, Slack, Airbnb, Asana and more. As for Angela, she largely focuses on investments in financial services and is currently a board member of Addi, SynapseFi, and Tally. Prior to a16z, Angela was a product manager at Google where she launched and grew Chrome for Android and Chrome for iOS into two of Google's most successful mobile products.
In Today’s Episode You Will Learn:
1.) How Angela made her way into the world of venture and came to be one of the leading fintech VCs with Andreesen Horowitz?
2.) Why does Angela believe that every company is going to be a fintech company? What is driving this shift? How does removing the barriers to entry for more products change both product quality and cost? How does Angela think about the role of regulation here?
3.) How does Angela think about what makes the best insertion points? How big does the initial wedge into the market have to be? When do you need to be able to prove you can transition from the insertion to the wider market? How does Angela fundamentally assess market size today?
4.) How does one transition to being the system of record? Do you have to be the system of record from day 1? Which examples are most striking for Angela on becoming a system of record? What are the biggest challenges in making this transition? Which metric tells you if you have become it?
5.) Does Angela think we are in a period of bundling or unbundling? What are the leading indicators of each? How does Angela assess the Fintech M&A market today? Will we continue to see large consolidatory moves in the form of Credit Karma, Plaid etc etc?
Items Mentioned In Today’s Show:
Angela’s Fave Book: Investing: The Last Liberal Art
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Alyson Friedensohn is the Founder & CEO @ Modern Health, a one-stop solution for employee mental well-being through evidence-based support and digital content. To date, Alyson has raised over $45M in funding from some of the best in the business including Kleiner Perkins, Founders Fund, John Doerr, 01 Advisors and Katrina Lake to name a few. Prior to founding Modern Health, Alyson was a Product Partner for Operations at Collective Health and before that was an operations manager @ Keas (acquired by Welltok).
In Today’s Episode You Will Learn:
1.) How Alyson made her way into the world of startups and came to change how we think about mental health with Modern Health?
2.) How does Alyson think about and assess her own psychology? How does Alyson deal with crisis modes? What works? What does not? What is the driver for Alyson to get her through the very toughest of times? How does Alyson approach her own attitude to risk?
3.) What is Alyson's biggest pieces of advice for non-technical founders? What are the biggest challenges Alyson has had to overcome as a non-technical founder? How did she do it? How did Alyson strategically invest in the sales process? What worked? What did not? How does Alyson think about the balance of hitting sales quota and mental health?
4.) With some of the best VCs in the world, how did Alyson approach the process of investor selection? What can VCs do to build that relationship of trust with their founders? How does multi-stage VCs investing impact whether the founder remains in a "sales process" for the next round? How does Alyson temper the weight of John Doerr's words?
5.) What have been Alyson's biggest lessons in making it work marrying another founder? What works? What is challenging? How do they as a couple think about switching off? How does Alyson advise Harry on his own love life?!
Items Mentioned In Today’s Show:
Alyson’s Fave Book: How to Win Friends and Influence People
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Kevin Hartz is Co-Founder & Partner @ A*, a newly listed special acquisition company which raised $200M to acquire and take public a tech startup. Kevin is also the Co-Founder, former CEO, and Chairman Eventbrite (NYSE: EB). Before Eventbrite, Kevin was the Co-Founder & former CEO of online money transfer service, Xoom (acquired by PayPal for $1.1B). Kevin is also one of the most successful early-stage investors in the business with a portfolio including the likes of Airbnb (Seed, Series A), Uber (Series B), Pinterest (Seed, Series A), Trulia (first check) and PayPal (Seed).
Troy Steckenrider is Kevin's co-founder and Partner @ A*. Prior to A*, Troy was COO @ ZeroDown changing the landscape for homeownership with $136M in funding. Before ZeroDown, Troy spent 5 years at Opendoor as Director of Capital Markets. Before that hyper-growth experience at Opendoor, Troy enjoyed roles at both Bain Private Equity and McKinsey.
In Today’s Episode You Will Learn:
1.) How Troy and Kevin came together to co-found A*? What is a SPAC? What are Kevin and Troy looking to achieve with the SPAC?
2.) What does Kevin believe are the primary drivers for the rise in SPAC's over the last few years? How will they change the structure of both the VC and startup industry? How will the SPAC landscape evolve over the next few years? What is the biggest challenge they face?
3.) Why does Kevin believe that the fee structure for SPACs is egregious? How would they like to change the incentive structure? How does the timeline for a SPAC transaction compare to that of an IPO? How does the fee structure compare when comparing SPACs to banks in IPOs?
4.) Why did Kevin and Troy choose $200M for the right size for their first SPAC? How does the size of the SPAC determine the type of company the SPAC will merge with? What are Kevin and Troy looking for in their partner company?
5.) What does the fundraising process look like for a SPAC? How do SPAC sponsors deal with the challenge that LPs call pull out if they do not like the proposed partner deal? When evaluating SPACs, what do investors look to invest because of? What makes A* special?
Items Mentioned In Today’s Show:
Troy’s Fave Book: Churchill: Walking with Destiny
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Jennifer Tejada is the CEO @ PagerDuty, the company that provides a real-time operations platform ensuring less downtime for your digital services. Prior to their IPO in 2019 PagerDuty raised funding from some of the best in the business including Accel, a16z, Baseline, Bessemer and Harrison Metal to name a few. As for Jennifer, prior to PagerDuty, she was CEO of Keynote Systems leading to their acquisition by Dynatrace. Before Keynote, Jennifer was Executive Vice President and Chief Strategy Officer at Mincom, leading them to their acquisition by ABB. If that was not enough, Jennifer is also on the The Estée Lauder Companies Inc. (NYSE: EL).
In Today’s Episode You Will Learn:
1.) How Jennifer made her way into the world of SaaS and came to be one of the leading enterprise CEOs today with PagerDuty? How does Jen advise graduates on joining a startup vs large incumbent?
2.) How does Jen analyse and evaluate her relationship to risk? What does Jen do to remove herself from her environment and make the clearest decisions? How has Jen's decision-making process changed? How does Jen encourage debate and free thought sharing internally?
3.) How does Jen think about the role of insecurity within leadership? What would Jen say are her biggest insecurities? How does Jen manage them and mitigate them today? What works? What does not? Why does Jen believe data is the key to overcoming insecurities?
4.) What have been Jen's biggest lessons on what successful board management looks like? What separates good vs great board members? How can CEO's structure their board in an optimal way? What do they need? What do they not need? How does scale change this?
5.) How does Jen think her style of leadership has changed over the years? What have been Jen's lessons on what it takes to both acquire and retain the very best execs? Where do many go wrong here?
Items Mentioned In Today’s Show:
Jennifer’s Fave Book: Tuesdays With Morrie: An old man, a young man, and life's greatest lesson
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Sahil Lavingia is the Founder and CEO @ Gumroad, the company that helps creators do more of what they love. With Gumroad, Sahil has raised funding from an all-star list of investors including Accel, Kleiner Perkins, First Round and then Max Levchin, Chris Sacca, Ron Conway and Naval Ravikant on the individual side. However, most recently Sahil has made waves launching one of the first rolling funds on AngelList with his being $6M per year. In the past, Sahil has backed the likes of Lambda School, Figma, HelloSign and Haus to name a few.
In Today’s Episode You Will Learn:
1.) How did Sahil make his way into the world of startups and angel investing? What were his biggest takeaways from being employee #2 at Pinterest? How did that experience impact his mindset?
2.) Why did Sahil decide to make his new fund an AngelList rolling fund? How is it structured? Does Sahil think this will represent a seismic shift in early stage investing? Is this a game of the 1%? Why does Sahil think early-stage remains so undervalued? How will this impact Series A pricing?
3.) How does Sahil assess his own price sensitivity today? How does Sahil think about the right way to turn down a founder? Where do many go wrong? How does Sahil feel about the rise of pre-empted rounds? How does Sahil advise seed founders with offers from multi-stage firms?
4.) What does Sahil believe founders care most about today in their investors base? How does Sahil think about investor brand and distribution? How does Sahil analyse the pros and cons of party rounds? How does Sahil advise founders on constructing their early cap table?
5.) How does Sahil think about his relationship to risk and to money? How did Sahil deal with it when his investors wrote off his company? How did Sahil feel about the weight of expectation placed on his shoulders at such a young age? How did he deal with this?
Items Mentioned In Today’s Show:
Sahil’s Fave Book: How to Win Friends and Influence People
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Ben Rubin is the Founder & CEO @ /talk, the anti-meeting tool for fast, decentralised conversations. Prior to co-founding /talk, Ben was the Co-Founder & CEO @ Houseparty, where he scaled the product to millions of users and raised over $70M in funding from the likes of Sequoia, Greylock and Entree Capital to name a few. In addition over the last few years Ben has enjoyed roles at Sequoia as a Scout and then also at Benchmark as an Entrepreneur-In-Residence.
In Today’s Episode You Will Learn:
1.) How Ben made his way into the world of startups and came to found Life on Air, later turning into Meerkat and Houseparty?
2.) What were Ben's key learnings from the Houseparty scaling experience? Why are the traditional metrics we use to measure startup success (DAU, MAU etc) insufficient? What is the nuance to metrics? How does Ben think about being first to market vs being the best to market?
3.) How does Ben believe the product principles differ when comparing the 0-1 stage vs 10-100 stage? How does Ben think about where to be rigorous on product? How does Ben advise founders to discover the key guiding product principle? What was it for Ben with Meerkat?
4.) Meerkat pivoted to Houseparty 3 months after having raised $40M, how did Ben communicate that to the board? How did they respond? How does Ben believe the best boards operate? What does Ben most look for in his board members? Where do many go wrong with board management?
5.) From the team side, when in hypergrowth, when do things start to break? What profiles are usually the first to break? Does that mean one should not hire those profiles? What can the leader do to create that intimacy and trust amongst the team?
Items Mentioned In Today’s Show:
Ben’s Fave Book: Seneca: The Shortness of Life
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Apurva Mehta is the Managing Partner @ Summit Peak Investments, investing in early stage venture capital funds and making direct co-investments. To date they have backed the likes of Raymond Tonsing, Lachy Groom and Josh Buckley to name a few on the fund side and then on the direct side, invested in Airtable, Virta Health and Sourcegraph. Prior to founding Summit Peak, Apurva spent 7 years as the Deputy Chief Investment Officer at Cook's Children's Hospital and before that spent 3 years as Director of Portfolio Investments at The Juilliard School.
In Today’s Episode You Will Learn:
1.) How did Apurva make his way into the world of fund investing? How did that lead to his founding Summit Peak and also becoming a GP?
2.) How does Apurva think about how much importance to place on references when diligencing managers? What reference types mean a lot? Which mean less? Why does Apurva still believe early-stage is the most inefficient segment of the venture landscape?
3.) How does Apurva think about GP commits? Is it fair to have a required benchmark? How does Apurva advise founders on LP concentration limits? When is one LP too much of a fund? How does Apurva advise managers on selling a stake in the management company?
4.) As a fund of funds, how does Apurva approach fund portfolio construction today? How does this differ between the fund portfolio vs the direct portfolio? How does Apurva think about the compression of fundraising timelines both with GPs and Founders? Why does Apurva believe founders at the early-stage care less about firm brand today?
5.) How does Apurva feel about investing in managers he has not met in person? How does the GP/LP fundraising process need to change? How does COVID change the fundraising process for venture funds? How will LPs react to these changes?
Items Mentioned In Today’s Show:
Apurva’s Fave Book: Principles: Life and Work by Ray Dalio
Apurva's Most Recent Investment: Sourcegraph
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Anna Khan is a General Partner @ CRV, one of the pre-eminent firms of Silicon Valley stretching over what is now an incredible 18 funds. In their portfolio, they have the likes of Airtable, Doordash, Postman and PillPack to name a few. As for Anna, prior to joining CRV, she spent an incredible 6 years at Bessemer investing in the likes of Intercom, NewVoiceMedia, RainforestQA and Zylo. If that was not enough, Anna is also the Founder & CEO @ Launch X Ventures, offering female entrepreneurs an immersive opportunity to learn how to raise capital for their businesses.
In Today’s Episode You Will Learn:
1.) How Anna made her way into venture as an analyst with Bessemer and how that led to her scaling the venture ladder to now being GP @ CRV?
2.) How does Anna feel about the importance of analysts in venture? Should founders spend meaningful time with analysts? How should they determine which to spend time with? What were the biggest lessons Anna learned about venture and people from being an analyst at Bessemer?
3.) With the rise of rounds being pre-empted, how does Anna determine when to lean in and move on a deal vs when to wait? How does Anna determine when to stretch vs be disciplined on valuation? Why does Anna believe very few firms are "doing real early-stage investing" today?
4.) Why does Anna believe that there are so much fewer women in venture? How does Anna respond to the suggestion that it is a "pipeline problem"? How would Anna advise an all-white male partnership looking to truly change how they work? How does carry come into showing commitment?
5.) What advice does Anna give to people on developing your early network? Why does Anna believe VCs spending time with VCs is antithetical? How has Anna's investment decision-making process changed over the last 9 years? How does Bessemer's compare to CRV's?
Items Mentioned In Today’s Show:
Anna’s Fave Book: Why We Sleep: The New Science of Sleep and Dreams
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Dev Ittycheria is the President and CEO @ MongoDB, recognized as the world's most popular next-generation database and the first database company to go public in over 26 years. Prior to their IPO, MongoDB raised from some of the best in the business including Sequoia, USV and NEA to name a few. As for Dev, before Mongo Dev was Managing Director at OpenView Venture Partners, Venture Partner at Greylock Partners, and CEO/Co-founder of BladeLogic, which was acquired by BMC for $900 million. Dev has also sat on some incredible boards including AppDynamics, athenahealth and BazaarVoice.
In Today’s Episode You Will Learn:
1.) How Dev made his way into the world of startups? How Dev made his entry into the world of venture? How that led to his joining Mongo as CEO?
2.) How has Dev seen his style of leadership change over the last few years? What are the 3 core benefits of being vulnerable with your investors? Why does Dev believe you sometimes have to be inefficient to be effective? What element/trait would Dev like to improve and develop as a leader?
3.) Where does Dev believe the majority of leaders make mistakes when it comes to scaling their teams and orgs? How does Dev think about the debate of whether to promote internally or hire externally for a role? Why does Dev believe the asymmetry of information there is dangerous?
4.) What has been Dev's biggest lessons when it comes to the speed that information is relayed within orgs? How does this differ between good news and bad news? What can leaders do to create environments where bad news is shared freely? Where do many go wrong here?
5.) How does Dev advise founders on the criteria they should use to determine which investors to work with? What has been so impressive to Dev about working with Sequoia? How would Dev describe Roelof Botha's style of board membership? How can investors crucially build trust with their CEOs?
Items Mentioned In Today’s Show:
Dev’s Fave Book: High Output Management
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Joe Thomas is the Founder & CEO @ Loom, the startup that helps you get your message across by making it easy to record instantly shareable videos. To date, Joe has raised over $68M from some of the valley's leading firms including Sequoia, Kleiner and Coatue as well as individuals such as Mathilde @ Front, Kevin & Mike @ Instagram and Dylan Field @ Figma to name a few. Prior to founding Loom, Joe was in LA as Director of Product at MyLife.com and before that Director of Operations at MediaPass. Due to Loom's success, Joe has been named to Forbes 30 Under 30 for Enterprise Tech.
In Today’s Episode You Will Learn:
1.) How Joe made his way from the mid-West to the valley and came to found one of the hottest startups today in Loom?
2.) What does Joe believe are 3 rules to operate remote teams successfully? Why does Joe believe in remote + HQ as a model so much? How do the tools and culture need to change with this as a new format for work? How do leaders now need to learn to write more than ever before?
3.) How has fundraising fundamentally change in the world of COVID? What are the benefits? What can founders do and tools can they use to increase their chances of getting funded in a COVID world? What did Coatue do to build rapport and trust without meeting in person?
4.) What advice would Joe give to founders on how to pick their early VCs? How does Joe advise founders when it comes to accepting multi-stage money at seed? Why does Joe believe you need to be upfront with your VCs about their ability to build future ownership?
5.) Sequoia and Coatue led the Series B, how did the round go down many months before Joe and Loom planned to raise it? What did Sequoia do to win and close the deal? How did that as a founder make Joe feel? How does Joe advise VCs on what it takes to win the most competitive of deals?
Items Mentioned In Today’s Show:
Joe’s Fave Book: Enders Game, Think On These Things
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Steve Jurvetson is the Co-Founder @ Future Ventures who announced their debut and flagship $200M Fund in 2019. Steve's incredible portfolio includes the likes of SpaceX, Tesla, Planet, Memphis Meats, Hotmail, and the deep learning companies Mythic and Nervana. Steve also sits on the board of both SpaceX and Tesla. Prior to founding Future, Steve was the co-founder of renowned valley firm Draper Fisher Jurvetson where he led investments in 5 companies that went public in successful IPOs and several others that became billion-dollar acquisitions.
In Today’s Episode You Will Learn:
1.) How Steve made his way into the world of startups and Silicon Valley and how that led to his creation of “The Lean Startup Movement”?
2.) How does Steve think about and assess market timing? How does Steve assess technical risk? Given the long term horizons of such deep tech projects, does Steve think we need to change the 10 + 2-year fund life structure? How would Steve like to see funds structured?
3.) Given the sheer size of outcomes if these plays work, how does Steve assess his own price sensitivity? How does Steve approach the challenge there is a lack of downstream investors for such deep tech projects? How does Steve try and catch an industry on the cusp of a transition?
4.) How does Steve assess his own relationship to money? How has it changed over the years? Why does Steve fundamentally believe that venture partnerships do not scale? Where do venture partnerships breakdown? How can one introduce cognitive diversity into a firm?
5.) Having worked with Elon Musk across both SpaceX and Tesla, what does Steve believe makes Elon one of the most gifted entrepreneurs of our time? What is Steve's most memorable moment from his many years of friendship with Elon? What have been his biggest takeaways from SpaceX and Tesla?
Items Mentioned In Today’s Show:
Steve’s Fave Book: Out Of Control: The New Biology of Machines, Social Systems, and the Economic World
Steve's Most Recent Investment: Prellis Biologic
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Clay Wilkes is the Founder & CEO @ Galileo, the API standard for card issuing and digital banking, powering many of the leading global FinTech companies including Chime, TransferWise and Monzo to name a few. Prior to their reported $1.2Bn acquisition by SoFi, Clay raised just $86M in funding with Galileo from the likes of Accel and Ryan Smith @ Qualtrics, having run the company as a profitable company before that for over 15 years. Clay also has a keen interest in philanthropy having created the Galileo foundation with his wife in 2005.
In Today’s Episode You Will Learn:
1.) How Clay made his way into the world of tech and startups more than 20 years ago and how he came to build the foundations for many fintechs today with Galileo?
2.) When looking at the current financial ecosystem does Clay believe we are in a phase of bundling or unbundling? Does Clay believe we will see the verticalisation of banking? Will every company become a payments company? Does Clay believe we will see consolidation in the space?
3.) What does Clay believe were the benefits of going 15 years withour raising VC money, building a profitable business? What are the trade offs? What could he have done if he had raised? With hindsight, does Clay wish he had raised earlier? Why was then the right time to raise?
4.) Why does Clay believe the discovery mechanism for VCs finding startups is broken? How did Clay select the venture firm he chose to work with, Accel? What advice does Clay give to board members when it comes to being the best board member to their founders?
5.) Why did Clay believe that selling to SoFi was the right decision? What are the benefits of the merger? How does Clay think about the competitive element that many of Galileo's current clients are competitors with SoFi? How do they remedy and solve for that today?
Items Mentioned In Today’s Show:
Clay’s Fave Book: Why Nations Fail: The Origins of Power, Prosperity and Poverty
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Brad Feld is a Co-Founder and Managing Director @ Foundry Group, one of the most successful venture firms of the last decade with a portfolio including the likes of Zynga, Fitbit and Sendgrid to name a few. Brad is also a co-founder @ Techstars and prior to Foundry, he co-founded Mobius Venture Capital.
Tracy Lawrence spent the last 8 years as Founder & CEO @ Chewse, the startup that it effortless for office managers to order delicious food for their teams. Tracy grew the team to 300 people across 4 markets, raised millions in venture capital, and ultimately sold the business to Foodee.
Jerry Colonna is the CEO of Reboot.io where he is now the professional coach to some of the world's leading founders. Prior to his work with Reboot, Jerry was an early-stage VC co-founding Flatiron alongside Fred Wilson in 1996.
In Today’s Episode You Will Learn:
1.) How did Brad, Jerry and Tracy all experience their first forms of depression? At what stage did it become a more prominent part of their life? Why do they think then was the catalyst?
2.) Why does Jerry believe that despite what people say, no one is crushing it? How can founders present their vulnerability as a strength? At what point did Tracy realise this? How did she convey her vulnerability to her team? Who is to blame for the lack of vulnerability and fear of opening up?
3.) How does Brad think about tying happiness to milestones? What are the biggest dangers of doing so? Does this mean one does not have goals? How does one balance between ambition and appreciating the present? How did Brad learn this when Amy asked for a divorce? How did he respond?
4.) Why does Brad believe fear, guilt and anxiety are useless emotions? What was the result of Tracy tying her mental state to her revenue line? How does Tracy think about the loneliness of being a founder? What does Brad believe is some of the biggest BS in the industry?
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Steve Blank is one of the leading luminaries of Silicon Valley, credited with being foundational to the creation of The Lean Startup movement and having spent the last 9 years at Stanford University as a professor and the last 8 as a Senior Fellow @ Columbia University. Steve is the author of "The Four Steps To The Epiphany" and "The Startup Owner's Manual". Prior to joining the world of academics and writing Steve spent over 20 years in the world of entrepreneurship as part of, or co-founded eight Silicon Valley startups ranging from semiconductors, video games, personal computers, and supercomputers. If that was not enough, Steve is also on the Defense Business Board for the United States Department of Defence.
In Today’s Episode You Will Learn:
1.) How Steve made his way into the world of startups and Silicon Valley and how that led to his creation of "The Lean Startup Movement"?
2.) Why does Steve vehemently disagree with Adam's Smith's "Invisible Hand" theory when it comes to government intervention? Why is this proven to have failed? How does this only help the rich become richer? As a result, what needs to change in the mechanics of the economy?
3.) Why does Steve not believe that there is accountability placed on investors and founders for projects they create and invest in? Why does Steve believe for the majority of investors today, they have no social conscience? How could this be changed and improved?
4.) How did seeing the booms and busts of the dot com and 2008 impact Steve's operating mentality? What are the 3 core traits that will ensure success for founders in a post COVID world? How should founders change their decision-making process post-COVID? Why does Steve believe in "benign dictatorship"?
Items Mentioned In Today’s Show:
Steve’s Fave Book: Innovator's Dilemma: When New Technologies Cause Great Firms to Fail
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Chamath Palihapitiya is Founder & CEO @ Social Capital, the organisation on a mission to transform society by using technology to solve the world’s hardest problems. Social's portfolio includes the likes of Slack, Yammer, Front, Intercom and Carta to name a few. As for Chamath, prior to founding Social, he spent an incredible 4 years at Facebook including as the original exec in charge of FB Platform as well as being responsible for overseeing core growth components and overseeing FB's mobile efforts. If that was not enough, Chamath is also an owner @ The Golden State Warriors & Chairman @ Virgin Galactic.
In Today’s Episode You Will Learn:
1.) How Chamath made his way into the world of tech and startups, came to be a VC with Mayfield before joining Facebook and then starting Social?
2.) What were Chamath's biggest takeaways from his team building the growth team at Facebook? Why does Chamath believe that forecasts are worthless? What should founders focus on instead? What did Facebook teach Chamath about defensibility and moat building?
3.) What was the realisation moment for Chamath that the venture firm he was building with Social was not what he wanted to build? Why does Chamath believe the biggest mistakes he made were "compensation and partner selection"? How would he do them differently now? What does he look for most in partners today? How does he detect for integrity?
4.) Why has Chamath doubled down on the SPAC model? What are the core benefits both to the founders and investors? What are the core challenges with both direct listings and IPOs? How does Chamath think about scaling his SPAC strategy? What are the core challenges in doing so?
5.) Facing alcoholism and psychological challenges with his parents, how did Chamath deal with becoming a carer sooner than expected? How has becoming a parent changed Chamath's operating mentality today? How does Chamath analyse his relationship to money today?
Items Mentioned In Today’s Show:
Chamath’s Fave Book: Liar's Poker: From the author of the Big Short
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Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Alex Mather is the Founder & CEO @ The Athletic, the startup bringing you in-depth sports stories you won't hear anywhere else. To date, Alex has raised over $139M with The Athletic from some of the best in the business including Founders Fund, Bedrock, Y Combinator and Emerson Collective to name a few. Before founding The Athletic, Alex spent an incredible 5 years as part of the hyper-growth @ Strava serving Vice President of Product Management and Product Design.
In Today’s Episode You Will Learn:
1.) How Alex made his way into the world of tech and startups with Strava? How did his time at Strava lead to his founding The Athletic?
2.) With the scaling of The Athletic to over 500 people, how has Alex seen his leadership style change and adapt? What does he need to improve? How did having children impact how he thinks about management? What lessons did he take from Strava on what worked for community building?
3.) What was it like raising money for a subscription media business back in 2016? Who was the first person to really take a bet on Alex and The Athletic? What value adds does Alex think are the most important for VCs to provide? What are the biggest investor misconceptions around media?
4.) How does Alex see the future structure of the media landscape? What elements of media is Alex most concerned about right now? Does Alex view Substack as competition? What does Alex believe will be the 2 ways to succeed in media moving forward?
5.) What have been the biggest customer acquisition learnings for Alex from The Athletic? How does Alex feel about platform reliance for customer acquisition with Facebook? What does it take to successfully acquire customers on Facebook at scale?
Items Mentioned In Today’s Show:
Alex’s Fave Book: The Kingdom of God is Within You
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Joe Lonsdale is a General Partner @ 8VC and in the past has invested in many notable companies including Wish, Oculus, Oscar and Guardant Health. As a result, in both 2016 and 2017, Joe was the youngest member of the Forbes 100 Midas List. Prior to 8VC, Joe co-founded Palantir, one of the world's most impactful multi-billion dollar software companies. Joe also co-founded and serves as Chairman @ Addepar, which has over $1.8 trillion managed on its wealth management technology platform. If that was not enough, Joe is also a founder of Affinity, Anduin and Esper.
In Today’s Episode You Will Learn:
1.) How Joe made his way into the world of tech and startups, came to co-found Palantir and Addepar and how that led to his founding 8VC? How does Joe
believe the study of history makes one a better investor?
2.) Why does Joe believe that the best VCs are company builders? How does Joe think about, evaluate and put into action the incubator model? How does Joe respond to LPs that suggest it is a distraction? How does voting for incubations differ for investment voting?
3.) What does contrarian thinking really mean to Joe? What does Joe do to specifically engender contrarian thinking in the 8VC partnership? What is the relationship between contrarianism and political correctness? How does Joe think about the dangers of woke culture today?
4.) How does Joe advise founders to think through cash burn and runway today? What is going to happen to companies that sacrified growth for gross margin in 1 year? How does Joe advise founders on the balance of sticking to your vision and mission vs knowing when to give up?
5.) Why does Joe think it is important to not just start new companies but new cities also? Despite the insane cost of living, why does Joe believe the Valley has given rise to the insane levels of innovation it has done? Will the dominance of the valley remain over the next decade?
Items Mentioned In Today’s Show:
Joe’s Fave Book: How Innovation Works, A Time to Build: From Family and Community to Congress and the Campus
Joe’s Most Recent Investment: Beacon
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Julia DeWahl is one of the rising stars of the Silicon Valley angel investor community with a portfolio including the likes of Linear (Sequoia-backed), Modern Fertility (USV backed) and Primer (Founders Fund backed). Prior to angel investing Julia was one of the first 10 employees at Opendoor seeing their hyper-growth first hand in many different roles from Head of Seller Experience to being General Manager of Pheonix & City Operations. Before Opendoor, Julia spent 3 years as a consultant at Bain. If that was not enough, Julia is also an avid cyclist and is setting up a women's cycling apparel line alongside her investing.
In Today’s Episode You Will Learn:
1.) How Julia made her way into the world of startups with Opendoor from Bain and how that position at Opendoor led to her angel investing? What were the 1-2 takeaways for Julia from her time at Opendoor that have most impacted how she angel invests today?
2.) Customer Discovery: When is the right time to engage in deep customer discovery work? How does one select the customers to go deep with? How does Julia structure the process? What questions are most revealing? Where do many go wrong? How does one determine the feedback to accept vs which to reject?
3.) How does Julia think about implementing systems for growth? What is the structure of these systems? Where does one start? How does Julia determine the metrics to track and focus on? How does Julia balance between growth vs profitability?
4.) Does Julia believe people can really scale with the company? What are the leading indicators that people are struggling to scale with the company? How does Julia advise generalists to survive and thrive in a scaling organisation? Should they specialise?
5.) What have been some of Julia biggest lessons of what it takes to be successful as an angel today? Who has Julia learned and gained the most from in this new discipline? How does Julia measure her own success as an angel? What are the core challenges?
Items Mentioned In Today’s Show:
Julia’s Fave Book: The Courage To Be Disliked: How to free yourself, change your life and achieve real happiness
Julia’s Most Recent Investment: Primer: Homeschool with superpowers
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Oren Zeev is the Founding Partner @ Zeev Ventures, one of the best and most under the radar firms in the early stage Silicon Valley landscape. Over the past decade, Oren has backed the likes of TripActions, Tipalti, Audible, Houzz, Chegg and Hippo Insurance to name a few. Prior to crushing it with Zeev Ventures, Oren spent 12 years as a General Partner @ Apax Ventures, starting in Israel and then moving to the US where he headed the Technology Practice of Apax and the Silicon Valley office.
In Today’s Episode You Will Learn:
1.) How Oren made his way into the world of venture with Apax and how that led to his founding his own firm, Zeev Ventures?
2.) Having been in a venture partnership, why did Oren want to be a solo GP? What are the benefits? How does it change decision-making? What are the downsides? How does Oren discuss deals and ideas without partners? How does Oren explain the decision to LPs on being a solo GP?
3.) Why does Oren not believe in thesis-driven investing? What are the dangers and downsides to it? Why do most managers still do it then? Why does Oren specifically look for under-appreciated markets? How is pricing and competition different there? How does Oren assess his own price sensitivity?
4.) Why does Oren think that diversification is overrated? How does Oren think about cross-fund investing? Why is it such a strength that managers should use? Why do many not do it? How does Oren think about reserve allocation? Why is he the only VC to not have a reserves strategy?
5.) How does Oren think about fund deployment timelines? Why do LPs not like the annual fundraising approach? How does Oren size up his position in companies over time and round? How does Oren feel about founders taking secondaries?
Items Mentioned In Today’s Show:
Oren’s Fave Book: The Last Lion: Winston Spencer Churchill: Defender of the Realm
Oren’s Most Recent Investment: Treeverse
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Lo Toney is the Founding Managing Partner @ Plexo Capital, a very unique firm making both direct investments and fund investments. They have invested in Precursor, Boldstart, Female Founders Fund and WorkBench on the fund side and then PlayVS, Replicated and StyleSeat on the direct side. Prior to Plexo, Lo was a Partner @ GV (Google Ventures) and before that was a Partner with Comcast Ventures where he led the Catalyst Fund. Before venture Lo was an operator enjoying exec roles at Zynga, Nike and eBay.
In Today’s Episode You Will Learn:
1.) How Lo made his way into the world of venture with GV and how that led to his innovating on the venture model investing in both funds and directly with Plexo today? What were Lo's biggest takeaways from his 5 years as a Partner @ GV?
2.) How will GPs raising today be impacted by COVID? How does this differ dependent on the stage they invest and the size of fund they are raising? How does Lo advise managers communicating with existing and new potential LPs today?
3.) What does Lo mean when he discusses your "minimum viable fund size"? How does Lo advise GPs when it comes to closing strategies? How much do they need for first close? How many closes should there be thereafter? Should they take the money when it is on the table?
4.) How does Lo feel about anchor LPs taking/investing in the GP? What are the benefits for the manager of doing so? Why does Lo believe there is such a binary view towards it? Why does Lo disagree with the benchmarks set of what a GP commit "should be"?
5.) Why does Lo believe we will see the hybridization of GP/LP over the coming years? What are the benefits of having your LP also direct invest? What are the core challenges to the model? How does Lo envisage the world of venture evolving over the next decade?
Items Mentioned In Today’s Show:
Lo’s Fave Book: Why Should White Guys Have All the Fun?: How Reginald Lewis Created a Billion-Dollar Business
Lo's Most Recent Investment: PlayVS
As always you can follow Harry and The Twenty Minute VC on Twitter here!