Marc Andreessen is a Co-Founder and General Partner at Andreessen Horowitz. The firm now manages over $90BN and has invested in the likes of OpenAI, Airbnb, Coinbase, Anduril and many more. Marc is an innovator and creator, one of the few to pioneer a software category used by more than a billion people and one of the few to establish multiple billion-dollar companies. Marc co-created the Mosaic internet browser and co-founded Netscape (sold to AOL for $4.2 billion). He also co-founded Loudcloud, which as Opsware, sold to Hewlett-Packard for $1.6 billion.
AGENDA:
05:00 — Why Introspection is Overrated: The Dangers of Learning from the Past
08:00 — The One Trait Marc Andreessen Looks For in Every Founder
14:30 — Are the Best Founders Broken? What Makes the Best Founders?
16:00 — “Extreme Ownership”: Why Everything Being Your Fault Changes Everything
19:00 — “Do You Read the Comments?” Fame, Criticism & How to Deal with Haters
26:00 — Is Venture Now Go Big or Go Home? The Real Future of VC
30:00 — Does Price Matter Anymore? The Dangerous Truth About Valuations
33:00 — “Stop Chasing Diamonds in the Rough”: Why Most VCs Get This Completely Wrong
36:00 — Do You Actually Need to Like Founders? The Uncomfortable Answer
40:00 — Are Companies 75% Overstaffed? The Most Controversial Take on Hiring
45:00 — When Will a16z Go Public?
50:00 — Why Labour Displacement Theory Around AI is Totally Wrong
55:00 — Why Silicon Valley Is More Dominant Than Ever?
01:00:00 — Why a16z Invested $300M into Adam Neumann
01:05:00 — What Still Drives Marc Andreesen?
01:10:00 — What is the Biggest Mistakes VCs Still Make Today?
AGENDA:
05:00 — Anthropic vs. OpenAI: Who Is Actually Winning the Enterprise War?
07:55 — "Air of Desperation": Is OpenAI Losing Its Invincibility?
18:00 — SpaceX at $2 Trillion: Elon’s Insane Plan to Build Data Centers in Space
29:00 — Jeff Bezos’ $100 Billion Fund: The End of "Doing It the Hard Way"
34:00 — The $20 Billion "Acqui-hire": The Groq Deal Broken Down
40:40 — Figma’s Death Spiral? Why the Markets Are Terrified of AI Disruption
56:00 — The Broken VC Math: Why You Need $1BN To Do Series A
01:04:00 — Win or Die: The Terrifying Reality of the Unicorn "Dead Zone"
Matthew Steckman is the President and Chief Business Officer of Anduril. Matt played a central role in securing the $20BN contract Anduril just won with the US military. Prior to Anduril, Matt served as Chief Revenue Officer for Zipline. Before Zipline, Matt held several leadership positions at Palantir.
AGENDA:
3:45 — Anduril’s $20BN Army Contract Broken Down
6:30 — What Do Most Defense Founders Get Completely Wrong?
9:15 — Can You Build a Billion-Dollar Defense Company Without the US?
12:05 — Why Government Contracts Are Brutal (And Why Most Fail)
15:40 — How Does Anduril Predict Wars 5–10 Years Before They Happen?
18:20 — Why Cyber Warfare Is the Most Dangerous Battlefield No One Understands
23:50 — Why There Will Only Be ONE Winning Drone Company
28:10 — How Anduril Decides Where to Deploy $100M+ Product Bets
35:20 — What Would Anduril Buy If They Had an Unlimited Checkbook?
41:10 — Why Anduril Must Go Public
45:00 — Quickfire: The Future of War, VC Mistakes & Career Advice
Shaunt Voskanian is the CRO @ Figma, where he has scaled the sales machine to over $1BN in ARR and over 400 people. Prior to Figma, Shaunt was Senior VP of Global Sales at Datadog where he scaled the revenue org to $1BN in ARR.
AGENDA:
04:33 - Are Great Sales Leaders Born or Trained?
06:55 - In a world of PLG, is sales less important than ever?
11:51 - Why does Shaunt not believe in traditional customer success teams?
14:31 - Does the role of the SDR survive in two years' time?
19:19 - When is the right time for sales to intercept in a PLG motion?
21:43 - How to Set Sales Quotas in a PLG AI Sales World?
31:19 - How has what you look for in sales hires changed over time?
42:54 - How do you judge sales performance if not on quota?
54:49 - Quick fire: Outdated sales tactic, What Role Dies, Best Sales AI Tool
Gokul Rajaram is one of the greatest operators turned investors of the last 2 decades. He is trusted as the go to advisor for the greatest founders in the world. Today he serves as a Board Director at three public companies: Coinbase, Pinterest and The Trade Desk. Prior to Marathon (his firm), Gokul served on the executive team at DoorDash and Block. Before Block, he served as Product Director of Ads at Facebook. Earlier in his career, Gokul served as a Product Management Director for Google AdSense. Gokul is also a prolific angel investor, having invested in 700+ companies, including Airtable, Figma, Groq, Runway, Supabase, and Vercel.
AGENDA:
03:53 — Investing Lessons from Google, Doordash and Facebook
05:32 — Why Mark Zuckerberg is the Greatest Distribution Genius Alive
07:23 — Why Every Company Today Needs to be Multi-Product
09:16 — Negative Gross Margins: Are the Best Companies Actually Built on "Shit" Economics?
10:50 — The SaaS Apocalypse: Is the Entire Sector Going to Zero?
12:15 — The 8 Moats of Enduring Software Companies: How to Analyse Companies
14:50 — Why Brand is No Longer a Strong Moat (And What Replaced It)
16:13 — Salesforce vs. Atlassian: Which Systems of Record are Dying?
18:13 — Outcome-Based Pricing: Is This the Total Death of Seat Pricing?
20:16 — The Bolt-On AI Trap: Why Rebuilding Your Entire UX is Non-Negotiable
23:44 — Are the Outcome Sizes of Vertical SaaS Large Enough for VC Today?
28:16 — The Zombie Cohort: What Happens to Private Companies with High Valuations?
32:44 — Is "King Making" Complete Bullshit?
34:21 — Durability Over Margins: What Really Matters in a 100x Growth World
35:36 — The Non-Consumption Miracle: Why Granola and Gamma are Crushing It
38:50 — The PayPal Rule: Can You Raise Prices 5 Times in 3 Years?
42:47 — My Biggest Miss: How I Misread the Shopify Billion-Dollar Mark
45:18 — The Courage to Bet: Why Instacart is the Best VC Deal Ever
46:33 — Seed vs. Growth Pricing: When Does Price Actually Destroy Returns?
50:53 — Does "Proprietary Founder Access" Even Exist?
54:33 — Double Down or Diversify? The Truth About Fund Reserves
59:44 — The Vanta Anti-Portfolio: A Mistake I'll Never Forget
01:01:21 — When to Sell: The "Sell a Third, Hold a Third, Trade a Third" Rule
01:04:12 — Why Remote Early-Stage Companies are Dying
01:07:33 — Why Mid-Level Partners are Fleeing Mega Funds
01:09:47 — The Best CEO Superpowers: Larry, Mark, Jack, and Tony
01:12:33 — The Next 10 Years: Why Dropouts are "AI Maxing" the World
Noam Lovinsky is the CPO @ Superhuman (formerly Grammarly). Prior to Superhuman he was a Senior Director of Product Management at Facebook. In his earlier years, he was CPO @ Thumbtack and spent 5 years as a Director of Product Management at Google where he was responsible for all of Youtube’s applications.
AGENDA:
03:43 What is Great Product Leadership in a World of AI
07:45 Does the Design Phase Die in a World of Vibe Coding
12:21 How AI Changes Product Development Most
22:23 Accelerating Product Development
29:32 AI's Impact on Product Building
34:19 Predictions for 2026
34:45 Quick Fire Round
38:41 Reflections and Future Plans
Ketty Slonimsky is Chief Growth Officer at Palta, the platform behind apps like Flo (the #1 female health app with 77M+ MAU), Simple, and Zing AI, where she leads a centralized growth function across the portfolio. She was previously first VP Product & Growth at HeliosX (£900M+ ARR, bootstrapped D2C healthtech), has advised companies like SonderMind, Runna, Guardio, Cheddar, P&G Digital Ventures, and is a board advisor at HeliosX.
AGENDA:
02:33 What is Growth and When to Hire For It
06:04 Three Profiles of Successful Growth Leaders
10:07 Challenges and Learnings from Failed Ventures
21:17 How to Optimise User Onboarding for Growth
26:14 Biggest Lessons on Retention
30:25 How to Artificially Create Organic Growth and Community Building
32:10 Why LTV Models are BS
37:35 How to Use Influencers to Grow Insanely Fast
47:07 The Metrics that Matter in Growth
49:48 Push Notifications and Engagement: What To Do vs What Not to Do?
51:57 Quick Fire Round
Anton Osika is the Co-Founder and CEO @ Lovable, the fastest growing company on the planet. In just 7 months, they have scaled from $0 to $120M in ARR. They have raised over $200M in funding from some of the best including Accel, Creandum and 20VC. Their latest round priced the company at a whopping $2BN.
Agenda for Today:
00:00 – Is AI an Arms Race… Or Just a Talent War?
03:45 – How Does Anton Compete with Zuck’s $100M Packages for Talent
07:30 – Founder Mode vs. Structure: Can Chaos Scale?
10:15 – The Brutal Truth About Defensibility in AI Startups
13:20 – Unit Economics: Are AI Companies Doomed to Bleed Cash?
17:00 – GPT-5: Game-Changer or Overhyped Disappointment?
20:10 – How Lovable Hit $100M ARR in Just 7 Months?
25:15 – Replit, Figma, Bolt: Which Competitor is the Best?
30:00 – The Security Bombshells No One Talks About
36:40 – Should Anyone Still Study Computer Science?
40:30 – Work-Life Balance Is Dead: Inside Anton’s 10x Culture
56:00 – OpenAI, Anthropic, or Grok: Who Wins the AI Wars?
Roger Ehrenberg is a Founding Partner @ IA Ventures, one of the most successful seed funds of the last decade with $475 million across their four funds. Previous investments include The Trade Desk, Datadog, Digital Ocean, Wise and Recorded Future. Most recently, Roger took a step away from the day-to-day running of the firm, since he started IA Sports Partners, investing in sports franchises and other sports-related assets. Last month, Roger, alongside his two sons, started Eberg Capital, an investment vehicle focused on web3, crypto, NFTs and next-gen infrastructure.
1.) How Roger made his way into the world of angel investing and venture having had a successful career on Wall St? How did seeing the booms and busts of the dot com and 2008 impact his investing mindset today? How does today compare to those times?
2.) The Investor Mindset:
3.) Investing Strategy:
4.) AMA:
Sarah Cannon is a Partner @ Index Ventures, one of the world’s leading venture funds with a portfolio including the likes of Dropbox, Skype, Figma, Bird, Slack and many more incredible companies. As for Sarah, at Index, she works with groundbreaking companies including Notion, Slack, Pitch, Quill and Instabase. Prior to Index Sarah spent time at CapitalG, Warburg Pincus and even worked in The White House as Policy Advisor for the National Economic Council.
Akshay Kothari is the COO @ Notion, the company that has taken the modern working world by storm as the all-in-one workspace to write, plan, collaborate and get organised. Just last week Notion raised a $50M round led by Index at a reported $2Bn valuation. Prior to Notion, Akshay spent 5 years at LinkedIn following his prior company, Pulse News, being acquired by LinkedIn in 2013.
In Today’s Episode You Will Learn:
1.) How did Sarah make her way into the world of venture from The White House and come to be a Partner @ Index today? How did Akshay parlay his angel investment into Notion into joining as COO the company 5 years later?
2.) With such a proliferation of collaboration tools today, how does Sarah see the remote work/collaboration tools landscape playing out? Are wein a phase of bundling or unbundling? Will we enter a phase of heavy consolidation? How does Notion think about the transition from an application to a platform? What are the challenges in doing so?
3.) What have been some of Akshay's core observations and learnings from watching the world move to remote work overnight? What behaviours will remain post COVID? What behaviours will not? What sectors will be forever changed due to the crisis? What opportunities does that bring about?
4.) Why did Notion decide to keep the team so small for so long? What are the advantages? How does Notion think about maintaining quality when hiring for scale now? What have been some of Akshay's biggest learnings in what it takes to attract A* talent to Notion?
5.) Why did Notion choose the route of profitability over the more conventional early path of the VC treadmill? How does one's mindset change when suddenly raising a large round of new financing? What becomes possible? What guard rails still need to be set?
Items Mentioned In Today’s Show:
Akshay’s Fave Book: Order without Design: How Markets Shape Cities
As always you can follow Harry and The Twenty Minute VC on Twitter here!
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Ryan Denehy is the Founder & CEO @ Electric.ai, the company that provides a world-class IT solution that's centralized, secure, and lightning-fast. To date, Ryan has raised over $37m in funding from some dear friends of the show in Rich @ GGV, Bessemer, Primary, Bowery, just to name a few. As for Ryan, he started his career at the tender age of 17 launching an action sports video production company, which was acquired just 4 years later. Ryan then spent 5 years at USA Today in numerous different roles. Following USA Today, Ryan started his second company, Swarm, acquired by Groupon just 3 years later.
In Today’s Episode You Will Learn:
1.) How Ryan made his way into the world of startups from launching an action sports video production company at the age of 17?
2.) Having founded 2 prior companies, would Ryan agree with Joe Fernande @ JoyMode in saying that "serial entrepreneurship is overrated"? What did he do right in the first 2 companies that he would look to do again? What did not work that he is avoiding? Where does Ryan most often see first-time founders make mistakes scaling?
3.) How does Ryan think about and assess wartime leadership? What is the right leadership style and approach to battle through the really tough times? Ryan's investors talk of his speed of execution, how does Ryan balance the speed with the quality when it comes to execution? How has Ryan seen both his role and the way in which he executes it change with the scale of the company and of himself?
4.) How does Ryan thnk about and assess forward planning when it comes to recruitment? How should this recruitment planning align to fundraising? Why must it start before the fundraise? How does Ryan think about levelling up individuals internally vs hiring external candidates? How does Ryan think about and present internal expectation setting?
Items Mentioned In Today’s Show:
Ryan’s Fave Book: Barbarians At The Gate
As always you can follow Harry, The Twenty Minute VC and Ryan on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Vlad Magdalin is the Founder & CEO @ Webflow, the startup that allows you to build better business websites, faster, without coding. To date, Vlad has raised over $73m with Webflow from some dear friends of the show including Accel, Ron @ Rainfall, Brianne @ Work Life, Benjamin Ling and Y Combinator to name a few. Prior to founding Webflow, Vlad was a Senior Software Engineer @ Intuit. Before Intuit, Vlad co-founded Chatterfox, a web application allowing people to stay in touch with groups of friends, family, or co-workers.
In Today’s Episode You Will Learn:
1.) How Vlad made his way into the world of startups? How did the original idea to democratise the world of design and site creation with Webflow come about?
2.) Webflow has had an unorthodox funding path with their recent $73m Series A, how was it for Vlad raising the seed round with Webflow? What lessons did he learn from that raise? Why did they drive to be breakeven so much earlier than others might? Why did Vlad believe now was the right time to go big and raise the Series A?
3.) Vlad chose to partner with Accel, what advice does Vlad give to founders in determining which funding partner to choose? What makes for the best VC <> founder relationships? What is the optimal way to build those relationships? Where does Vlad believe that VCs can strategically move the needle? Where do many think VCs can really help but they most often cannot?
4.) What have been Vlads biggest lessons when it comes to successful board management? What advice would Vlad give Harry when it comes to joining boards as new board member? What does Vlad mean when he says, the best board members come to the board with the mindset of "servant leadership"? How do they show that in their actions? How can investors create an environment of trust at the board?
5.) Vlad AMA: Why does Vlad believe that it is a distraction for founders to be angel investing alongside their role as a founder? How does he believe this creates a wedge between them and the team? How has having kids impacted how he thinks about operating today? What have been the big takeaways from fatherhood?
Items Mentioned In Today’s Show:
Vlad’s Fave Book: Leaders Eat Last: Why Some Teams Pull Together and Others Don't
As always you can follow Harry, The Twenty Minute VC and Vlad on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Matt Harris is a Partner @ Bain Capital Ventures, a leading US venture fund with a portfolio that includes the likes of LinkedIn, Lime, SendGrid, Jet.com and more incredible companies. As for Matt, he specialises in financial technology and services and has led investments in the likes of Acorns, OpenFin, SigFig, Ribbon and Billtrust. Prior to joining BCV, Matt founded Village Ventures, which he ran for 12 years and where he focused on early-stage fintech investing. Before Village Matt actually started his investing career Bain Capital private equity in 1995.
In Today’s Episode You Will Learn:
1.) How Matt made his way into the world of venture from private equity and what led him to specialise as he has done in the world of fintech?
2.) How did seeing the boom and bust of the dot com impact Matt's investing mindset today? How has Matt's fear of the cyclicality of markets actually lost him a lot of money in the past? What has that taught Matt on trying to time markets? What were the main takeaways for Matt from running his own firm? How does it differ to a partnership?
3.) Why does Matt believe we are seeing late-cycle momentum investing today? What is the evidence to suggest this? How does Matt think about the right cadence to invest through market cycles? What does Matt mean when he says, "Series A valuation does not matter anymore"? Why? How does Matt assess his own price sensitivity today?
4.) Why does Matt believe that investing in improbable ideas is a good strategy? What does this mean the internal investment decision-making process looks like at Bain? Why is full consensus sometimes a concern? How does Matt approach market sizing? Why does it not matter at Series A? When does it really start to matter?
5.) Matt has said before that "backing sociopaths can work". What did he mean by this? What founder type does Matt most like to back? Does one have to manage the relationship with them very differently to other founder types? What are the acceptable risks vs unacceptable risks with this founder type?
Items Mentioned In Today’s Show:
Matt’s Fave Book: The Third Plate: Field Notes on the Future of Food
Matt’s Most Recent Investment: Finix
As always you can follow Harry, The Twenty Minute VC and Matt on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Immad Akhund is the Founder & CEO @ Mercury, the startup that makes bank accounts that help tech companies scale. To date, Immad has raised funding from some of the best in the business including a16z and CRV on the fund side and then individuals including Elad Gil, Airtable's Howie Liu, Plaid's Zach Perret, Naval Ravikant, Justin Kan and OpenDoor's Eric Wu. Prior to founding Mercury, Immad held enjoyed numerous different roles including being a part-time partner at Y Combinator and then also founding HeyZap, building developer tools for mobile game developers, ultimately acquired in 2016.
In Today’s Episode You Will Learn:
1.) How Immad made his way from studying in the UK to being a YC Partner in 2017 and building one of the valley's hottest startups today in the form of Mercury?
2.) What does Immad want to do differently this time around with Mercury vs his time with HeyZap? What 1-2 mistakes that he made the first time round is Immad looking to avoid? How does being a serial founder impact one's ability to acquire the best talent? What does Immad think is harder the second time around? How has becoming a parent changed the way that Immad thinks about founding and building companies?
3.) How does Immad approach the process of picking the idea? What was the specific process with Mercury, step by step? Why does Immad believe it is an advantage to not have a background or prior career in the space you are looking to innovate in? What advice does Immad have for founders looking to move into highly regulated industries?
4.) How does Immad approach and assess the element of competition? What is the right way for founders to present competition when pitching to investors? Why is a 2x2 matrix the wrong approach? What does Immad advise portfolio founders he has invested in with regards to competition and the landscape in front of them?
5.) What have been some of Immad's biggest learnings from making over 120 angel investments? How has angel investing specifically helped certain parts of how he thinks about operating and being a founder today? What advice does Immad give with regards to investor updates? What makes the best ones? What makes the worst? How often should they be?
Items Mentioned In Today’s Show:
Immad’s Fave Book: The Accidental Superpower: The Next Generation of American Preeminence and the Coming Global Disaster
As always you can follow Harry, The Twenty Minute VC and Immad on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Daniel Kan is the Chief Product Officer @ Cruise, the company building cutting-edge hardware and software that work seamlessly together to transform the way we all experience transportation. In 2016, Cruise was acquired by GM for a reported $1Bn. Since the acquisition Cruise has raised $7.25 billion in committed capital and has attracted SoftBank, Honda, and T. Rowe Price as investors. As for Daniel, he started his career at a startup called UserVoice. He then founded Exec, an on-demand hospitality service company, and successfully sold Exec to Handy. As a result of his many success, Daniel was listed as number 7 on Fortune’s 2016 40 under 40 list for the most influential people in business.
In Today’s Episode You Will Learn:
1.) How Daniel made his way into the world of startups and came to co-found the game-changing company of the next movement mega wave of transport innovation in Cruise?
2.) What have been Daniel's biggest lessons on what works for leaders in scaling themselves? How can a leader ensure their team feel real ownership and accountability for their roles? How does Daniel think about KPI and goal-setting? How does Daniel look to strike the balance between ambitious but achievable goals and then unrealistic?
3.) How does Daniel think about micro-management? Is there ever a time for it? What are the leading indicators you or someone on the team is micro-managing? What can they do to correct it? What are the dangers of micro-management? How does Daniel think about assessing human potential in terms of a stretch VP and a stretch too far?
4.) Why does Daniel believe that "if you are not growing, you are dying"? What has been transformational to Daniel in increasing his own level of self-development and learning? How does the organisation need to be set up to ingest these learnings in real-time and improve? Where do many go wrong when it comes to mistakes and learnings?
5.) At acquisition, Cruise had just 40 team members, today the team consists of 1,460. What have been some of Daniel's biggest lessons in the process of scaling the team with such rapidity? What have been some of the core challenges? How has Daniel's style of leadership had to change and evolve with the growth?
Items Mentioned In Today’s Show:
Daniel’s Fave Book: Shogun: The First Novel of the Asian saga: A Novel of Japan
As always you can follow Harry, The Twenty Minute VC and Daniel on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Dave Sobota is the Vice President of Corporate Development @ Instacart, the company that delivers your groceries in as little as 1 hour. To date the company has raised over $1.9Bn in funding from some of the very best investors and operators including Mike Moritz @ Sequoia, Jeff Jordan @ a16z, Aaron Levie @ Box, Sam Altman, Garry Tan and more incredible names. As for Dave, prior to Instacart, he was Director of Corporate Development @ Google for over 10 years and before that was with leading law firm, Wilson Sonsini.
In Today’s Episode You Will Learn:
1.) How Dave made his way from the world of law to Director of Corporate Development at Google to his position at Instacart today?
2.) In 2016, we had 513 BC backed exits, 499 were M&A, so how does Dave assess the M&A landscape today? Why id Dave bullish on the future M&A environment, at least for the next 12 months? Where are his concerns around M&A clustering? How does Dave view the entrance of large scale PE into the tech M&A arena?
3.) From leading Google's M&A practice, what have been Dave's core learnings on whether an entrepreneur should sell their company or remain independent? Paul Graham once said, "startups only talk to corp dev when they are doing really well or really badly". Does Dave agree? What are the reasons a startup would not speak to corp dev? What is the right way for them to communicate this while leaving the door open for future conversations?
4.) How does Dave operationalise the tracking of the startup market and determine what startups he wants to meet? How does Dave like to and think about working with the VC community here? What does that relationship building process look like? In those early meetings, what are the core questions that founders must ask? How much of a role does price play for Dave when considering an acquisition?
5.) How can founders ensure when they sell their company, that it will be properly integrated? What answers from the acquirer suggest it will or will not be? From countless M&A processes, what do the best integrations look like post-acquisition? Where are mistakes often made? Does Dave agree with Paul Graham in stating it is a "gruelling" process?
Items Mentioned In Today’s Show:
Dave’s Fave Book: Lonesome Dove
Dave’s Most Recent Acquisition: Tenor
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.
Jeff Russakow is the CEO @ Boosted, the startup producing vehicle grade electric skateboards rethinking how we travel. To date, they have raised $74m in funding from the likes of Khosla Ventures, iNovia Capital, Andreessen Horowitz and our friends at Initialized. Prior to Boosted, Jeff was CEO @ Gimbal where he doubled revenue in his first year and added 80 new enterprise clients. Before that, Jeff was the CEO @ Findly where he grew the company to 450 employees and 20m end users. Jeff also enjoyed prior roles with the likes of Symantec, Adobe, SAP and Yahoo.
In Today’s Episode You Will Learn:
1.) How Jeff made his way from leading enterprise CEO to re-thinking the way we travel today as CEO of Boosted?
2.) How does Jeff analyse the current sentiment to fundraising in the valley, specifically with regards to business construction? How has Jeff seen the investor class fundamentally transition over the last 20 years? When approaching investor selection, what is the 1 question that Jeff always asks? Where do founders often make mistakes here?
3.) Having raised the $60m round in 2018, how does Jeff approach the theme of capital efficiency today with Boosted? How does Jeff determine when is the right time to pour fuel on the fire? Why is Series B often the most challenging phase when considering the focus on unit economics and vision simultaneously?
4.) What is Jeff's gut reaction to the statement, "hardware is hard"? Why does Jeff feel this to be a glib statement that misses the point? How does Jeff respond to the criticism of the commodity element of hard, easy to replicate and copy? How would Jeff like to see the investor class change their mindset to hardware? What is the right way to approach it?
5.) What are the core elements required for a successful CEO transition? For a potentially incoming CEO, what must they be wary of with regards to the information conveyed to them by investors of the company? Where has Jeff seen many go wrong in CEO transitions? What can the founders do to make this process as smooth as possible?
Items Mentioned In Today’s Show:
Jeff’s Fave Book: The Missing Piece
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.
Adam Pritzker is the Chairman & CEO @ Assembled Brands, a holding company providing working capital and financial services to emerging brands. In October 2018, they raised $100m in development capital from the prestigious Oaktree Capital Management. As for Adam, he is also a co-founder of General Assembly where during his tenure, prior to its acquisition by Addecco Group, he served as Chief Creative Officer, Chief Product Officer, and Chairman. For his entrepreneurial endeavors, Adam was featured in Forbes’ 30 Under 30, Vanity Fair’s The Next Establishment, Inc. Magazine’s 30 Under 30, and Business Insider’s Silicon Alley 100.
In Today’s Episode You Will Learn:
1.) How Adam made his way into the world of startups with the co-founding of General Assembly and how that led to his founding Assembled Brands and financing the future of brands?
2.) Why is Adam optimistic about the current state of the consumer brand and retail environment? How does Adam respond to Alex Taussig @ Lightspeed's suggestion of the "re-platforming of retail"? How does Adam approach the changing demographic of consumer spend? What does this mean for both the brands and the channels they use to acquire customers? Does Adam believe we are in a consumer bubble today?
3.) How does Adam think about the lack of free and open distribution today for consumer companies? Are the traditional channels now too expensive to acquire customers on? How does Adam advise consumer founders on the saturation rate of marketing channels? How can they foresee the ceiling ahead of time?
4.) Adam has previously stated that Instagram is the new QVC, what did he mean by that? What type of consumer brand is Instagram best suited for? Why does Adam believe that in many cases the venture financing method is suboptimal and wrong for these scaling brands? What can founders who have taken VC funds and now seen it was potentially a mistake do?
5.) Why does Adam believe that the "infrastructure to power emerging brands is broken"? How can the current stack and infrastructure for brands be improved? What metrics should consumer founders really hone in on today? What sort of metrics suggests a brand is VC backable vs is not VC backable? How does Adam think about the ability of the consumer brand space to provide venture returns at scale?
Items Mentioned In Today’s Show:
Adam’s Fave Book: (1.) The Coddling of the American Mind: How Good Intentions and Bad Ideas Are Setting Up a Generation for Failure. (2.) The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It
Adam's Most Recent Investment: Felix Gray
As always you can follow Harry, The Twenty Minute VC and Adam on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Anand Sanwal is the Founder & CEO @ CB Insights, the tech market intelligence platform that ingests massive datasets, to answer complex questions and predict future trends. CB is the 9th best place to work in the US according to GlassDoor and one of the fastest growing SaaS companies in the US. To date, CB Insights has raised over $11m in VC funding, a topic Anand discusses at length in our episode today! Prior to founding CB, Anand held numerous roles at American Express including running a $50m Innovation Fund and managing the company's discretionary investment spend ($4-5Bn p.a.). Before American Express, Anand was one of the early team @ Kozmo.com, one of the most well-funded and infamous startups in NYC history.
In Today’s Episode You Will Learn:
1.) How Anand came to found CB Insights from running American Express' $50m Innovation fund and the a-ha moment there?
2.) Why does Anand believe that revenue funding is the best kind of funding? What 3 elements does Anand believe it fundamentally allows? What does Anand mean when he says "most have 3 masters, you can only serve two of them at once"? Does Anand believe that founders today are treating their investors as customers?
3.) How does Anand distinguish between business that can be funded from revenue vs those that cannot? How does Anand think about the relationship between growth and margin? Why does it make sense for VCs today to push for the suggestion that startups need to raise big to grow? How can founders think about and respond to this?
4.) Why does Anand believe that most B2B content today is crap? What are the core pillars that make great B2B content today? How does Anand think about potentially going too far when it comes to the risque nature of the content? What advice would Anand give to B2B founders wanting to ramp up their game in content? Where do many go wrong?
5.) What does Anand mean when he says that "pedigree is often overrated"? How has that led Anand's thinking when building out the team at CB? Where does Anand see most founders make mistakes when it comes to both team and company scaling? What interview question does Anand find most revealing of an individuals' character?
Items Mentioned In Today’s Show:
Anand’s Fave Book: Influence: The Psychology of Persuasion
As always you can follow Harry, The Twenty Minute VC and Anand on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Danny Rimer is a Partner @ Index Ventures, one of the world's leading venture funds with a portfolio including the likes of Dropbox, Skype, King, Bird, Slack and many more incredible companies. As for Danny, he is known for his investments in Dropbox, leading the company's Series B, Etsy, King (makers of world famous, Candy Crush), Skype and more recently many retail and fashion businesses such as Farfetch, Glossier and GOAT. He's been on the coveted Forbes Midas List for more than a decade and in 2017 was appointed an Officer of the Order of the British Empire (OBE) for services to business and charity and the New York Times included him in its list of the top 20 venture capitalists worldwide.
In Today’s Episode You Will Learn:
1.) How Danny made his way into the world of venture and came to be a Partner @ Index Ventures?
2.) Having backed the likes of King, Skype, Glossier, how does Danny respond to Peter Fenton and Jeremy Levine's suggestions of a "consumer downturn"? Does Danny believe there is a lack of free and open distribution today? Can startups compete with such inflated CACs? Henry Davis @ Glossier asks: how have you seen acquisition models change over time? How do you envision acquisition models of the future?
3.) Peter Fenton said on the show previously, he always laughs when he hears VCs say they like big markets, how does Danny assess market sizing today? What have been Danny's biggest lessons on assessing market size when looking at his portfolio? How does Danny think about niche markets today in such an Amazon dominant world? How does Danny assess price today? How does Danny determine when to stretch vs stay firm?
4.) Having helped many companies scale to global success, what does Danny believe to be the core considerations in getting your startup ready for global expansion? How did Danny find Index's expansion when opening up their first US office in 2011 in SF? What were some of the biggest challenges? How does Danny think about and assess generational transition within venture and Index more specifically today?
5.) Danny has spent over 3,000 hours on boards to date, how has Danny seen himself evolve as a board member over that time? What were some inflection moments in those hours that fundamentally changed the way Danny thinks? What advice would Danny give me, having just gained my first institutional board seat?
Items Mentioned In Today’s Show:
Danny’s Fave Book: Killing Commendatore by Haruki Murakami
Danny’s Most Recent Investment: Goodeggs
As always you can follow Harry, The Twenty Minute VC and Danny on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Laura Deming is Founding Partner @ The Longevity Fund, the first VC firm dedicated to funding high-potential longevity companies. To date, Laura has raised $26m across 2 Longevity funds and has backed the likes of Unity Biotechnology, Precision Biosciences, Metacrine, Navitor, and Alexo Therapeutics. Prior to Longevity, Laura was accepted to MIT at the age of 14 to study physics and then dropped out to join the Thiel Fellowship and start The Longevity Fund. If that wasn't enough, Laura most recently founded Age1, a four-month startup accelerator program focused on founders creating longevity companies.
In Today’s Episode You Will Learn:
1.) How Laura made her way from studying physics at MIT at just 14 to founding The Longevity Fund and dropping out to join The Thiel Fellowship?
2.) As a 16-year-old, looking to raise a fund to invest in longevity, how was the fundraise process for Laura? Why does Laura believe that raising your first fund is very much like raising a seed round for a company? What was the catalytic moment when the fundraise started to come together? What were the biggest challenges of the raise?
3.) Why does Laura believe that there is a shortage of young biotech founders today? What can be done to solve this and increase pipe? How does Laura find biotech founders compare to more traditional consumer and B2B founders she engages with? How does what they look for from their investor base differ?
4.) Laura has spoken before of "the importance of going against the herd"? How does Laura assess the current landscape for biotech investing? Is Laura concerned to see the entrance of much more traditional VCs into the space? How does Laura look to try and avoid groupthink? What is crucial to this?
5.) How does one need to think about portfolio construction when investing in an inherently riskier biotech space? Does Laura agree with the conventional wisdom around the lack of follow-on funding for biotech companies? How does Laura think about reserve allocation with Longevity today?
Items Mentioned In Today’s Show:
Laura’s Fave Book: The Mysterious Stranger by Mark Twain,
Laura’s Most Recent Investment: System1
As always you can follow Harry, The Twenty Minute VC and Laura on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Linda Xie is a Co-Founder & Managing Director @ Scalar Capital, one of the leading crypto asset funds to have been born over the last few years with Linda becoming one of the most prominent figures in the space. Prior to co-founding Scalar, Linda was a product manager at Coinbase where she worked with regulators and law enforcement. Before Coinbase, she was a portfolio risk analyst at AIG. If that was not enough, Linda is also an advisor to 0x, the critical infrastructure layer in the emerging financial stack built on a foundation of Ethereum token standards.
In Today’s Episode You Will Learn:
1.) How Linda made her move into the world of crypto joining Coinbase back in 2014 and how that led to her founding of Scalar? What were her biggest takeaways from seeing the first-hand scaling of Coinbase?
2.) What is a privacy coin and why does it matter? What are some of the dominant legitimate uses for privacy coins? From ZCash to Monero to Dash, there are many players in the space, what are some of the core benefits and tradeoffs of each platform? What is the fundamental problem with privacy coins today?
3.) What is a decentralised exchange, why does Linda believe it is inherently important? How does Linda assess the current exchange environment today? Where does she see it moving over the coming years? What have been some of Linda's biggest learnings advising 0x? Given the mission and ethos of crypto, does Linda believe that centralised exchanges fundamentally go against the core ethos of the space?
4.) How does Linda perceive the state of ethereum today? What are some of the core challenges facing ethereum today? How does ethereum compare to alternative smart contract platforms? What is their differentiation? Will we see a winner take all/most market within smart contract platforms? Will we see smart contract platforms be regionally fragmented?
5.) How does Linda address the fundamental challenge of valuing tokens today? What has been her preferred model in doing this to date? How does Linda assess the mega raises we have seen over the last year? How does Linda think about preventing projects from raising huge rounds just to stay in step with the mega raises of their competitors?
Items Mentioned In Today’s Show:
Linda’s Fave Book: Sapiens: A Brief History of Humankind
Linda’s Most Recent Investment: Kadena
As always you can follow Harry, The Twenty Minute VC and Linda on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Shabih Rizvi is the Founding Partner @ Gradient Ventures, Google’s new AI-focused venture fund, which will invest in and connect early-stage startups with Google’s resources, innovation, and technical leadership in artificial intelligence. Prior to Gradient, Shabih was a Partner at KPCB, where he was actively involved with investments in TrueCaller, Mobcrush, Veem and Ujet. In addition, he helped the firm build their seed program and served as advisor to Flipagram and Victorious. Before KPCB, Shabih founded and led the startup outreach program for Google Play. Prior to Google Play, Shabih worked on the Mobile Apps Lab team which built SMB products. His primary focus was scaling TalkBin (Acquired by Google) to enterprise clients. Shabih joined Google after Google’s acquisition of AdMob, where he was a manager on the Business Development team.
In Today’s Episode You Will Learn:
1.) How Shabih made his way into the world of venture with Kleiner Perkins and how he came to be a Founding Partner @ Google's AI focused venture fund, Gradient? What were Shabih's greatest lessons from working side by side with John Doerr?
2.) Shabih has said to me before "founder relationships and their longevity really matter". What does Shabih mean by this? How has this played out for Shabih in an investing environment? What have been Shabih's subsequent learnings?
3.) How does Shabih identify the "3 buckets" that VCs source from? How does Shabih look to filter through opportunities at scale? What must he see in the deck? What are his quick no's? What is Shabih's framework for saying no both with efficiency and kindness? Why does Shabih believe this is one of the hardest parts of the role?
4.) What does the internal investment decision-making process look like at Gradient? Why do they believe that 2 partner meetings a week is optimal? Prior to that, how does Shabih structure his meetings with founders? Why does Shabih believe it is so important to go to them at their HQ? Should all investors go to the founder?
5.) Why is Shabih a strong believer in the decentralisation of talent away from the valley? What are the primary drivers for this decentralization? How does Shabih think about pricing in different regions? To what extent does it differ wildly? How does Shabih respond to traditional SaaS wisdom that you have to build your SaaS business in the valley?
Items Mentioned In Today’s Show:
Shabih’s Fave Book: Measure What Matters, When Breathe Becomes Air
Shabih’s Most Recent Investment: Scotty.ai
As always you can follow Harry, The Twenty Minute VC and Shabih on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
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Andrew Farah is the Founder & CEO @ Density, the startup that measures real-time occupancy of every room in your office. To date, they have raised over $16m in funding from some great friends of the show in the form of Founders Fund, Mark Suster @ Upfront, Ludlow Ventures, Jason Calacanis, Hiten Shah and Arjun Sethi, just to name a few. As for Andrew, prior to founding Density, he was a Managing Partner @ Rounded, a software development agency & product studio. There, Andrew and the team built the first Density prototype.
In The Show Today:
1.) How Andrew made his way into the world of technology and product with Rounded and came to found the people counter of the next generation in Density?
2.) How does Andrew view the role of super-connectors today? What specific time has a super-connector really moved the needle for Andreq and changed the trajectory of Density? What can one do to first build relationships with these people? What can be done to sustain that relationship and really engage and deepen it?
3.) How does Andrew view the importance of "employee retention" in the ultimate success of a company? Density have never had an employee leave in 4 years, what does Andrew believe they have done right? What has not worked for them? What does he mean when he says, "the best leaders answer employees questions before they are asked"?
4.) What has Andrew found to be the commonalities in the truly special VCs? What do they do that makes them so special? How do they view the world and the assessment of companies that is so right? How does Andrew think about investor selection? Where does Andrew see many founders going wrong with this?
5.) Why does Andrew think that so many hardware startups fail today? What do they consistently underestimate and not understand? What are the core challenges in building a global supply chain? How does one have to think about cost of goods (COG) and unit economics when scaling hardware startups?
Items Mentioned In Today’s Show:
Andrew’s Fave Book: The Idea Factory: Bell Labs and the Great Age of American Innovation
As always you can follow Harry, The Twenty Minute VC and Andrew on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
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Barry Eggers is a Founding Partner @ Lightspeed, one of the world’s leading venture funds with a portfolio that includes the likes of Snapchat, Mulesoft, Affirm, StitchFix, AppDynamics, Nutanix and many more incredible companies. Barry himself has led investments in Snapchat, Metasolv Software (acquired post-IPO by ORCL), Calista Technologies (acquired by MSFT), Arbor Networks (acquired by DHR), Growth Networks (acquired by CSCO). As a result of his incredible success, Barry has been named to Forbes Midas List numerous times. Prior to VC, Barry held executive roles at Cisco Systems where he established many of the company’s largest distribution channels across OEMs, Service Providers, Distributors, and VARs. He also developed Cisco’s initial M&A process and directed the first wave of acquisitions and integrations for the company.
In Today’s Episode You Will Learn:
1.) How Barry made his way from the world of Cisco to the wonderful world of venture and came to found one of the most successful firms of the decade in Lightspeed?
2.) How does Barry break up the development of the venture ecosystem into 3 distinct stages? What does Barry believe have been the positive changes? What does Barry believe have been the negative changes? Does Barry believe there is an excess supply of capital today? Why does Barry believe there are too many first time funds? What is the outcome?
3.) Did Barry always aim to build the multi-stage, multi-geography firm that he has built with Lightspeed, from the start? What have been the fundamental inflexion points for Lightspeed both in the increase in brand value and liquidity to LPs? Why does Barry believe building a firm really is an art? What should managers most look for in their first LPs?
4.) What does Barry believe are the 3 ways a venture firm can fail in a generational transition? How can firms incentivise young partners to see the career path and trajectory ahead? What must the older partners at the firm be willing to do? What have been Barry's biggest lessons in their successful generational transition?
5.) Barry has sat on boards for over 21 years, how has Barry seen himself develop and evolve as a board member over time? What makes a truly functional board? What are the best practices? Who is the best board member Barry has ever sat on a board with? What makes Jim Goetz such a special board member?
Items Mentioned In Today’s Show:
Barry’s Fave Book: Quantum Computing: A Gentle Introduction (Scientific and Engineering Computation)
Barry’s Most Recent Investment: Audius
As always you can follow Harry, The Twenty Minute VC and Barry on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.