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

The Twenty Minute VC takes you inside the world of Venture Capital, Startup Funding and The Pitch. Join our host, Harry Stebbings and discover how you can attain funding for your business by listening to what the most prominent investors are directly looking for in startups, providing easily actionable tips and tricks that can be put in place to increase your chances of getting funded. Although, you may not want to raise funding for a startup. The Twenty Minute VC also provides an instructional guide as to what it takes to get employed in the Venture Capital industry, with VCs giving specific advice on how to get noticed from the crowd and increasing your chances of employment. If that wasn't enough our amazing Venture Capitalists also provide their analysis of the current technology market, providing advice and suggestions on the latest investing trends and predictions. Join us so you can see how you can get BIG, powerful improvements, fast. Would you like to see more of The Twenty Minute VC, head on over to www.thetwentyminutevc.com for more information on the podcast, show notes, resources and a more detailed analysis of the technology and Venture Capital industry.
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Now displaying: 2020
Oct 22, 2020

Eoghan McCabe is a technology entrepreneur. He's started a number of companies, the most notable of which is Intercom, the conversational relationship platform. He was CEO of Intercom for nearly 10 years, during which he grew the company to hundreds of millions in annual revenue, nearly 700 employees, and raised nearly $250M from the likes of Kleiner Perkins, Index, Bessemer, and ICONIQ. He's also invested in dozens of companies including Stripe, Figma, SuperHuman, and Coda. In the summer of 2020 he moved to the role of Chairman of Intercom.

In Today’s Episode You Will Learn:

1.) How Eoghan made his way into the world of startups from Ireland and came to build one of the Valley's greats with Intercom?

2.) How does Eoghan thinking about living and thriving with a chip on one's shoulder? What does Eoghan advise in terms of one's search for their true selves? What were his biggest learnings in his search? What does Eoghan advise people who maybe feel they have lost themselves?

3.) Having been CEO of a $Bn company for close to 10 years, how does Eoghan think about dealing with the weight of expectation placed on shoulders? How did he manage it? How does he think about his identity being so tied to his company?

4.) In terms of being one's authentic self, how can one achieve this while also respecting their stakeholders who may hold different views? How does Eoghan think about being an authentic leader vs bowing down to the demands of your team? What is the right balance?

5.) Why does Eoghan think that vision can actually be limiting? How does Eoghan think about stress testing one's vision and ambition? What adversity from early VCs did Eoghan have to fight against? How does Eoghan encourage dissent and debate within his teams?

Items Mentioned In Today’s Show:

Eoghan’s Fave Book: Breathe: simple breathing techniques for a calmer, happier life

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

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

Oct 19, 2020

Cyan Banister is one of the most successful and renowned early-stage investors of the last decade. Her portfolio includes the likes of SpaceX, Uber, Affirm, Opendoor Postmates, Niantic and Thumbtack to name a few. Today Cyan is a Partner @ Long Journey Ventures, joining the team there following a 4-year stint @ Founders Fund where she led deals in both Niantic and HQ Trivia. Prior to Founders Fund, Cyan was a super successful operator and angel, co-founding Zivity and before that being an early employee at Ironport, leading to their acquisition by Oracle.

In Today’s Episode You Will Learn:

1.) How Cyan made her way into the world of startups? How SpaceX came to be her 1st angel investment? How that led to her joining the world of VC?

2.) How does Cyan think about and assess her relationship to money? Why does someone believe she had a fear or loathing of money? What made Cyan the capitalist she is today? How does Cyan analyse her relationship to risk? Has Cyan always trusted her own convictions?

3.) How does Cyan think about her own investment decision-making process? What were Cyan's biggest lessons from her experience with HQ Trivia? How did she change how she interacts with founders pre-investment? Why does Cyan never Google someone before meeting?

4.) How does Cyan think about price sensitivity today? Why does she believe there will be a reckoning? How will this shake out in terms of who succeeds and who fails? Why is Cyan in favour of party rounds? How does she think about VCs with sharp elbows?

5.) Why does Cyan believe SF is eating itself? What can be done to reinvigorate the city positively? What can be done to solve much of the homelessness problem? Why does Chesa Boudin never convict anyone? Why does Cyan believe her "BLM tweet is not spicy"? Why is Cyan fundamentally sad and worried for the current state of the world?

Items Mentioned In Today’s Show:

Cyan’s Fave Book: Snow Crash

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.

 
 
Oct 16, 2020

Spike Lipkin is the Founder & CEO @ Newfront Insurance, the modern insurance brokerage empowering risk management experts with advanced technology to deliver innovative solutions to their clients'. To date, Spike has raised from some of the best in the business including Founders Fund, Meritech and 20VC Fund. Prior to founding Newfront, Spike was one of the first employees at Opendoor, where he helped grow the team from 5 people to an enterprise value of over $5Bn today. Prior to Opendoor, Spike was an investor at Blackstone, where he served on the startup team that built Invitation Homes into the largest owner of single-family real estate in the United States.

In Today’s Episode You Will Learn:

1.) How Spike made his way from banking to be one of the first operators at Opendoor to founding the next generation of insurance with Newfront?

2.) What were some of the biggest takeaways for Spike from his time at Opendoor as employee #5? How does Spike approach prioritisation? How does he determine what to delegate vs what to control?

3.) How would Spike describe his own style of leadership? How has Spike needed to change his style with the business? What does Spike believe is his biggest weakness as a leader? What is he doing to confront it and grow as a leader? What is the most important thing a leader can do?

4.) How does Spike think about what it takes to acquire the very best talent? What does his framework for hiring look like? Why did Spike decide to hire a COO? Why was then the right time? How does Spike think about the balance between hiring external vs promoting internal?

5.) Why did Spike believe it was important not to announce any of his prior fundraises? How did Spike approach investor selection with Newfront? Does Spike believe founders should meet with VCs between fundraises? Which angel has done the most to move the needle for the company? How?

Items Mentioned In Today’s Show:

Spike’s Fave BookTeam of Rivals: The Political Genius of Abraham Lincoln

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.

Oct 12, 2020

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. As for George, today at the firm he focuses on advancing health through revolutionary computer science, centred around bio-engineering. During his incredible 16 year tenure at CRV, he has led deals in the likes of PillPack, Udacity, Scribd and HealthIQ. Before joining CRV, George was a General Partner @ Mohr Davidow Ventures for over 6 years.

In Today’s Episode You Will Learn:

1.) How George made his way into the world of venture over 21 years ago and how he came to be a General Partner @ CRV 16 years ago?

2.) How did seeing the booms and busts of the dot com and 08 impacts George's investment mindset? What is the right way to voice concerns in an internal investment discussion? How does George now view capital intensity? How does it impact his conviction and check size?

3.) Why does George believe one should invest in founders who do not need their investors help? Why does George believe the best founders have experienced some form of parental instability? How does George detect the psychological need to win when he meets founders? What are the signs?

4.) How would George describe his own philosophy of board membership? How has it changed over time? What are the 2 control functions that a board member has? What advice does George give to new board members today? Where do many young board members make mistakes?

5.) How does George analyse his own personal relationship to money? How has it changed over the years? How did his relationship to money change his relationship with people? Was that challenging? How did he cope with it? How does he advise others who experience the same?

Items Mentioned In Today’s Show:

George's Favourite Book: Foundation Trilogy

George’s Most Recent Investment: Glympse Bio

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.

Oct 8, 2020

David Lawee founded CapitalG, Alphabet’s independent growth fund, in 2013, drawing on his experience both at Google and as a serial entrepreneur. Since then, he has helped transform high-potential startups into some of the most highly valued businesses of our generation, including Airbnb, Lyft, Snap, Robinhood, Credit Karma, Oscar, Lending Club and Thumbtack. Prior to CapitalG, David played a pivotal role in Google’s growth story--first as Google’s Chief Marketing Officer and then as the instrumental VP of corporate development where his group spearheaded over 100 acquisitions for the company.

CLICK TO LISTEN ON ITUNES

In Today’s Episode You Will Learn:

1.) How David made his way into the world of startups, came to be the first CMO @ Google and how that led to his founding CapitalG?

2.) Having operated and invested through both the dot com and 08', how has seeing the booms and busts impacted David's investing mindset? How does David think about temporal diversification today with CapitalG? Why does David believe diversification is largely overrated?

3.) How does David think about portfolio construction today, given CapitalG is a growth fund? How does David compare early-stage to growth today? How does David think about loss ratios at growth? How does David benchmark good vs great from a multiple perspective at growth?

4.) How does CapitalG approach investment decision making today? How does David avoid consensus thinking/following the crowd when it comes to deals? Why does David believe investment clubs operate much more successfully than partnerships? How does that change the structure for CapitalG?

5.) How has David seen himself evolve and develop as a board member of the years? What type of board member would David say he is today? How does that change with the founder? Who is the most memorable board member David has sat on a board with?

Items Mentioned In Today’s Show:

David’s Fave BookBorn A Crime: Stories from a South African Childhood 

David’s Most Recent Investment: Albert

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.

Oct 5, 2020

Arlan Hamilton is the Founder and Managing Partner @ Backstage Capital, the seed fund that has paved the way investing exclusively in startups that are led by underrepresented founders. Backstage Capital also expanded their model and now have Backstage Accelerator working with companies across 4 cities. Last month, Mark Cuban gave Arlan $6M to invest in underestimated founders (ArlanWasHere Investments Fund I). Arlan is also an Author of "It's About Damn Time". If you would like to invest with Arlan, you can, check out BackstageCrowd.com with over 2,000 accredited and non-accredited investors, they just completed their 6th deal and $1m raised within 3 months of launch.

In Today’s Episode You Will Learn:

1.) How Arlan made her way from the airport floor to founding her own venture firm, Backstage Capital and writing a book, "It's About Damn Time"?

2.) How does Arlan assess her own relationship to money and wealth? What is Arlan's thinking around her desire to give away 90% of her wealth? How does Arlan evaluate her own appetite for risk? How has that changed over time?

3.) From a strategic perspective, what are some core elements to Arlan's strategy that are not obvious? What are the main misconceptions that remain with regards to under-represented founders? What does Arlan believe are the leading indicators when assessing founders today?

4.) What does Arlan believe have been the biggest challenges in building the firm that is Backstage? What have been the core breaking points in the scaling of people and strategy? How does Arlan think about the relationship between brand vs reputation? What does Arlan believe are the main misconceptions people have about her?

5.) How would Arlan like to see the world of venture change over the next decade? What can LPs do to encourage more under-represented founders are backed? How can this be measured? Who should be held accountable?

Items Mentioned In Today’s Show:

Arlan’s Fave BookWhat I Know For Sure by Oprah Winfrey

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.

Oct 1, 2020

Katherine Boyle is a Partner @ General Catalyst, one of the leading venture firms of the last decade with a portfolio including the likes of Stripe, Snapchat, Airbnb, Canva, Cazoo, the list goes on. As for Katherine, at GC she has led deals in game-changing companies such as Anduril, Nova Credit, Spring Discovery and Airmap to name a few. Prior to General Catalyst, Katherine entered the world of venture with Founders Fund and before that spent an incredible 4 years at The Washington Post where Katherine investigated entrepreneurship in many forms.

In Today’s Episode You Will Learn:

1.) How Katherine made her way from investigating entrepreneurship at The Wall St Journal to being an intern at Founders Fund to today, being a Partner @ General Catalyst?

2.) Why does Katherine believe that journalism is like venture? Why does Katherine believe there are two different styles of venture? What were Katherine's biggest takeaways from her formative years in venture with Founders Fund? How did that impact her investing mindset?

3.) What does Katherine mean when she says she "invests solely on founder narrative fit"? Are there leading indicators of this fit? What advice did Katherine take from her conversation with Mike Moritz pre VC career? How does Katherine strategically avoid consensus thinking and decisions?

4.) How does Katherine approach market sizing? How does Katherine think about strategic insertion into niches that expand to much larger markets? How does Katherine assess market timing? How does Katherine determine the velocity of a market tailwind? What is an example of this?

5.) How does Katherine evaluate the rise of pre-empted rounds today? What advice does Katherine give to founders considering taking multi-stage money at seed? Why did it make sense for Anduril? How does Katherine gain the time of the founders when they are not raising?

Items Mentioned In Today’s Show:

Katherine’s Fave BookThe Decadent Society: How We Became the Victims of Our Own Success

Katherine’s Most Recent Investment: Ophelia

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.

Sep 28, 2020

Palmer Luckey is the Founder @ Anduril Industries, founded on the premise of radically transforming the defence capabilities of the United States and its allies by fusing artificial intelligence with the latest hardware advancements. To date, Palmer has raised over $385M with Anduril from Founders Fund, a16z, Elad Gil, Spark Capital, Lux Capital, General Catalyst and 8VC to name a few. Prior to changing the world of defence, Palmer founded Oculus VR where he designed the Oculus Rift. Oculus VR was acquired by Facebook for $2.3Bn in 2014.

In Today’s Episode You Will Learn:

1.) How Palmer made his way into the world of startups, made his way from trailer to selling Oculus for $2.3Bn to changing the defence industry with Anduril today?

2.) How does Palmer evaluate his own relationship to money? How has that changed since his $2.3Bn Oculus exit? How does Palmer assess his relationship to risk? How does Palmer approach the correlations between money, risk and happiness?

3.) What were some of Palmer's biggest takeaways from his time scaling Oculus? How have they informed his mindset with Anduril? What worked? What did not work? How has Palmer changed as a leader? How does Palmer approach personal development? How does he optimise for it?

4.) Palmer scaled Oculus to 1,400 people in 1 year, where do organisations break with scale? Why does Palmer believe, "you never want to play yourself"? Where does he feel his biggest weakness is as a scaling leader? How does Palmer approach hiring at scale yet maintaining culture?

5.) From a defence standpoint, why does Palmer feel the US needs to be more like the Chinese? Why is the DoD so poor at investing in innovation? What does it take to sell into the DoD really effectively? Why have the only 2 successful defence companies been founded by billionaires?

Items Mentioned In Today’s Show:

Palmer’s Fave Book: The Three-Body Problem

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.

Sep 25, 2020

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 

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.

Sep 21, 2020

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

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.

Sep 18, 2020

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?

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.

Sep 14, 2020

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?

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.

Sep 11, 2020

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

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.

Sep 8, 2020

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

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.

Sep 4, 2020

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).

CLICK TO LISTEN ON ITUNES

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

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.

Aug 31, 2020

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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Aug 28, 2020

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).

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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 BookTuesdays With Morrie: An old man, a young man, and life's greatest lesson

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Aug 24, 2020

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 BookHow to Win Friends and Influence People

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Aug 21, 2020

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

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.

Aug 17, 2020

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 BookPrinciples: Life and Work by Ray Dalio

Apurva's Most Recent Investment: Sourcegraph

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

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Aug 14, 2020

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 BookWhy We Sleep: The New Science of Sleep and Dreams

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Aug 10, 2020

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

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

Aug 7, 2020

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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Aug 3, 2020

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 BookOut Of Control: The New Biology of Machines, Social Systems, and the Economic World

Steve's Most Recent Investment: Prellis Biologic

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.

Jul 31, 2020

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:

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