Paige Finn became interested in venture capital during college, but within a year and a half of graduating in 2020 she already has a fund!  In this episode you will learn: 1. How she secured her first allocation before having a fund 2. The steps she took to set up an SPV while being a non-accredited investor 3. How she raised a $1.6m fund 4. Behind Genius' investing thesis and strategy 5. The books that have most influenced her work and writing style 6. Why she wrote a picture book (for adults) called "Seed to Harvest: A Simple Explanation of Venture Capital"

Packy McCormick turned his massive newsletter into a Not Boring Fund I in 2021, and has since invested $10M into startups. In this episode you will learn: 1. How Packy raised his first fund from his readers.  2. What regulations he needed to navigate to comply with the SEC.  3. Which sectors he invested his first $10M into (in just 6 months) and some of his breakout startups.  4. Why IRR can be hilariously large in the early stages of a small fund. 5. How he manages a syndicate and a venture fund while still doing right by LPs.

David’s been a VC for a while, but he just launched a new $2.8M fund part-time with Nat Manning. We get into why his small fund size is actually so significant and represents new possibilities in venture plus: - How he uses his podcast and community to get dealflow - What he thinks you need before starting your own VC fund   https://twitter.com/djrosent

Mac the VC joins the show as the first guest for Angel Season 6 to share his story and how he invests.    https://twitter.com/MacConwell

Check out Gotham Gal Ventures: https://gothamgal.com/investments FOLLOW Joanne: https://twitter.com/thegothamgal FOLLOW Jason: https://linktr.ee/calacanis Show notes: 1:07 Jason intros "The Gotham Gal" Joanne Wilson & they reminisce on the '90s in New York & magazines 5:04 Spotting a bubble, issues with raising above your performance, New York during the pandemic & returning to normal 11:43 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist 13:12 New York's pre-pandemic situation, healthcare detaching from employment 16:11 Rethinking education & commercial real estate, NYC's pro-development mindset, roasting Hudson Yards 24:50 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel 26:19 Impact of high-end residential real estate on NYC 29:22 Joanne's experience investing in underrepresented founders, how the industry has changed over the past 15 years, opportunity with underrepresented founders 36:16 Assure - Get 20% off your first SPV at http://assure.co/angel 37:50 Why Joanne slowed her investment pace during the peak market, sorting process with an influx of startups, portfolio management in an unsustainable market 44:47 Reasons for startup failure, advice for founders raising large amounts of capital 56:14 Family talk, NFTs & sketchy art market dealings

Check out Panoramic Ventures: https://panoramic.vc Check out SoftBank's Opportunity Fund: https://theopportunityfund.com FOLLOW Paul: https://twitter.com/pauljudge FOLLOW Jason: https://linktr.ee/calacanis Listen here: Apple: https://podcasts.apple.com/us/podcast/this-week-in-startups-audio/id315114957 Spotify: https://open.spotify.com/show/6ULQ0ewYf5zmsDgBchlkr9 Overcast: https://overcast.fm/itunes315114957/this-week-in-startups-audio Thanks to our partners: Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist OurCrowd - Sign up for a free account at https://www.ourcrowd.com/twist LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel Show notes: 1:05 Jason intros Paul Judge & they discuss the Miami startup scene & the impact of investing over Zoom 11:37 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist 13:08 How Paul invests, rebranding to start Panoramic Ventures & joining the investment board at SoftBank's $100M Opportunity Fund 17:26 Are dedicated opportunity funds the right approach to maximize funding of underrepresented founders? Where underrepresented founders have an edge 24:34 OurCrowd - Sign up for a free account at https://www.ourcrowd.com/twist 26:11 Jay-Z's insane Q1, why George Floyd resonated more than prior policy brutality videos 35:11 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel 36:47 Downstream investors looking for underrepresented founders 41:33 Celebrity/influencer funds impact on the future fundraising landscape 43:53 What makes it easy for Paul to invest: "What's your Olympic Team?", anti-portfolio 53:07 Paul's greatest hits as an investor, paradox of borrowing money as a rich person 1:00:20 Educating more people on entrepreneurship via reality TV, Jason's Clubhouse crusade, future of SF

Check out Initialized: https://initialized.com FOLLOW Garry: https://twitter.com/garrytan FOLLOW Jason: https://linktr.ee/calacanis Show notes: 1:08 Jason intros Garry Tan & they talk about Garry's Posterous regrets & lessons from failure, going from seed-stage to growth-stage founder 8:33 Garry on life as an investor, Paul Graham's original YC content/community funnel 11:04 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel 12:39 Garry's YouTube experience, investing in Clubhouse & the social audio space & Jason's Clubhouse beef 20:27 Twitter spaces coexisting with Clubhouse, Twitter's recent product groove, Initialized's investment in Clubhouse 28:05 Assure - Get 20% off your first SPV at http://assure.co/angel 29:40 How accelerators get great value, Capital-as-a-Service, equity participation as newer generations' north star 36:37 Sweet spot age for founders, ISAs & community-driven learning 39:13 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist 40:44 VCs moving downstream & missing the early-stage orchard, potential new models to provide value, avoiding sharp elbows as a seed investor 48:58 Garry explains Alexis Ohanian leaving Initialized & their continued bond as friends 53:55 Unicorn patterns, understanding important consumer metrics

Check out Automattic: https://automattic.com FOLLOW Matt: https://twitter.com/photomatt FOLLOW Jason: https://linktr.ee/calacanis Show notes: 1:07 Jason intros Matt Mullenweg & they discuss starting WordPress & getting into angel investing 5:47 Angel investing in the early 2000's as ecosystem building & charity, Automattic's SPAC potential, potential for individual properties to spin out 11:48 OurCrowd - Sign up for a free account at https://www.ourcrowd.com/twist 13:14 How WooCommerce compares to Shopify, open-source flexibility, thoughts on running a public company, difficulty of the media business 20:17 Audrey Hepburn's influence on Matt 21:30 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel 23:03 Matt's first big hits as an investor, holding on to winners 28:15 Practical uses for crypto, being bullish on the technology of crypto, impact of bad actors on decentralized systems 34:30 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist 35:48 Policing speech on the Internet, Trump stress test, analyzing Trump's ban 48:17 Pioneering remote work, future in a post-COVID world, advantages in competing for top talent, middle management's disadvantages due to remote work 59:37 Future of San Francisco, managing hybrid in-person / remote, tips for new founders

Check out Greylock: https://greylock.com FOLLOW Reid: https://twitter.com/reidhoffman FOLLOW Jason: https://linktr.ee/calacanis Show notes: 1:07 Jason intros Reid Hoffman & they discuss the Joby Aviation VTOL SPAC, VTOLs vs. self-driving 11:53 Assure - Get 20% off your first SPV at http://assure.co/angel 13:26 Reid on setting up the meeting between Peter Thiel and Mark Zuckerberg, hitting a 20000x+ with Facebook, opportunities for sustained growth in the big tech reaches population limitations 18:02 When business leaders should speak up on certain issues 23:50 Reinstating Trump's accounts 25:15 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel 26:50 Anti-portfolio: Reid tells the story of missing on Stripe, is ownership % overrated? 36:12 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist 37:31 Navigating potential portfolio conflicts 40:59 Lessons from hitting on Airbnb with his first investment at Greylock 49:15 Passing on SpaceX after an Elon pitch, returning billions to LPs in one investment 54:28 Reid's process for being a world-class investor, breaking down the Clubhouse investment 1:01:08 Investing over Zoom, future of Silicon Valley & San Francisco, Reid's next act

FOLLOW Mark: https://twitter.com/mcuban FOLLOW Jason: https://linktr.ee/calacanis Thanks to our partners: Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist OurCrowd - Sign up for a free account at https://www.ourcrowd.com/twist LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel Show notes: 1:04 Jason intros Mark Cuban & they discuss the circumstances of their first meeting, Mark's dot-com bubble hedge, resurgence of retail investors 9:30 Mark's prescient bets, origin of Blog Maverick 12:20 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist 13:39 Understanding naked shorts, how shorts could be a companies best friend 17:15 Story behind Mark venturing into the movie business, producing the Enron documentary with a day-and-date release, thoughts on MoviePass & vertical integration in the film industry, risks of investing in AI 25:14 OurCrowd - Sign up for a free account at https://www.ourcrowd.com/twist 26:46 How AI is starting to impact the NBA, what's changed over the past 20 years since Mark bought the Dallas Mavericks 33:40 NBA getting into wagering 36:23 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel 37:55 Mark's relationship with the NBA, player-fan interaction, Porzingis trade & pairing him with Luka 44:59 Mark's original consulting business, diversity in tech, investing in Arlan 48:33 How Mark reviews cold emails, how crypto plays into the future of the NBA: smart contracts, digital assets, non-fungible tokens 57:32 How DeFi can change finance forever, Knicks talk, vaccine optimism

FOLLOW Howard: https://twitter.com/howardlindzon FOLLOW Jason: https://linktr.ee/calacanis Thanks to our partners: Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel Assure - Get 20% off your first SPV at http://assure.co/angel Show notes: 1:22 Jason intros Howard Lindzon & they talk about angel investing stories from the first dot-com bubble 5:50 Creating the $ cashtag on Twitter, psychology of public vs. private investing, why VCs fled the public markets after the dot-com bust & how this relates to the SPAC movement 12:51 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist 14:23 Are recent public market returns sustainable? Why hedge fund VCs have an advantage, how the Tinder swipe relates to SPACs 23:27 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel 24:58 How SPACs are a hedge against paternal investing laws, why active investors should push back against "set and forget" investing, how index funds enable poor executive performance 29:51 The "Great unbundling" of index funds, how Howard invested in Robinhood 34:08 Assure - Get 20% off your first SPV at http://assure.co/angel 35:41 Howard tells a Robinhood term sheet story 39:26 Deconstructing the unprecedented Robinhood situation 48:22 Pandemic, vaccine news, optimism, how the party moved from private to public markets 55:21 Disney as a conglomerate, pure-play stocks, Apple's narrative issues, investing over Zoom, Uber's recent acquisition 1:05:50 Creating a digital wall with China, Trump's Twitter ban

Check out Elad's Website: http://eladgil.com FOLLOW Elad: https://twitter.com/eladgil FOLLOW Jason: https://linktr.ee/calacanis Thanks to our partners: OurCrowd - Sign up for a free account at https://www.ourcrowd.com/twist LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist Show notes: 0:00 Start 1:05 Jason intros Elad Gil, Elad explains what he's learned since he started angel investing 10+ years ago, Internet market caps growing 10X-30X over the last decade, software's surface area 11:32 OurCrowd - Sign up for a free account at https://www.ourcrowd.com/twist 13:06 Understanding Clubhouse's valuation, a history of "overpriced" standout social apps, monetization options 19:01 Potential of paying it forward to black creators 25:01 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel 26:32 SPACs, startups going public earlier, theories on why "stay private longer" was popular in the 2010s and why 2020s looks like the "go public faster" decade 33:11 Thoughts on selling secondary shares & selling in public markets 36:04 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist 37:36 How the pandemic endgame impacts his investment thesis, Israel's incredible vaccine distribution 47:07 Elad's thesis: product-market driven OVER team driven, importance of market pull in non-obvious markets, using growth rate to determine market size 54:34 Amazon's sustained growth rate, how consumer companies accelerate at scale, big tech's best acquisitions 1:00:49 Self-driving, VTOLs, future tech epicenters, work from home

Check out Intercom: https://www.intercom.com FOLLOW Des: https://twitter.com/destraynor FOLLOW Jason: https://linktr.ee/calacanis Thanks to our partners: LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist Assure - Get 20% off your first SPV at http://assure.co/angel Show notes: 0:00 Start 1:08 Importance of charging for enterprise products from the start 6:08 Explaining the phenomenon of startups that become great companies when the idea behind them is not logical or the market is unforeseen 10:18 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel 11:49 Investing in Notion - what he initially saw in the product, how UI helps Notion stand out, how angel investing & giving advice help hone his skills as an operator at Intercom 17:39 Common fundraising mistakes that founders make 21:48 Growth planning at a late-stage startup 24:26 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist 25:57 How Intercom was initially pitched, the singularity of CRM platforms (Salesforce, HubSpot,Intercom, etc.), preparing for IPO & raising capital as a late-stage startup 30:52 Operating profitably, thoughts on acquisitions as a route to growth 35:02 Assure - Get 20% off your first SPV at http://assure.co/angel 36:32 Hopin's rapid rise in online events, dealing with the pandemic and being cooped up, keeping up company moral 44:13 Intercom's international offices, work from home, Slack's market penetration play, Microsoft vs. Salesforce in the 2020's 51:09 Acquisition offers, why hasn't Intercom sold yet? Pricing power in the enterprise, important product-market fit metrics 1:01:50 Thoughts on going public Subscribe to our YouTube to watch all full episodes: https://www.youtube.com/channel/UCkkhmBWfS7pILYIk0izkc3A?sub_confirmation=1 Subscribe to TWiST Clips for all the best moments: https://www.youtube.com/channel/UCS7tJlcUA6PzVHEMo-X7ddg?sub_confirmation=1

Check out BoxGroup: https://boxgroup.com FOLLOW David: https://twitter.com/davidtisch FOLLOW Jason: https://linktr.ee/calacanis Show notes: 0:00 Start 1:04 Jason intros BoxGroup's David Tisch & they discuss being an angel investor post-Great Recession & starting Open Angel Forum 7:36 David on investing his own money until 2019 & why he decided to raise from LPs, investing in 350+ companies 10:45 Odoo - Get your first app free & $1000 off your first implementation pack at https://odoo.com/twist 12:18 Expectations in a 350+ company portfolio 16:36 Investing in Plaid: Why he invested, how he met the founder, where do they go from here 23:22 LinkedIn Jobs - Post your first job free at https://www.linkedin.com/angel 24:53 Big winners for BoxGroup so far, 10% of investments driving most of the returns, huge feedback loops in early-stage investing 31:01 Dealing with bad investors in the middle tier, importance of reputation 34:46 OurCrowd - Sign up for a free account at https://www.ourcrowd.com/twist 36:23 How David interacts with portfolio founders regarding advice & company-building, judging the experiment & founder instead of the company itself 41:51 Ownership concentration, taking pro-rata, dealing with sharp-elbowed investors 49:38 How Lee Fixel personifies the low-profile, incredibly reputable investor 52:34 How mentality changes when investing your own money vs. other people's money, pattern recognition on founders, rarity of depth of talent 1:03:59 Thoughts on WeWork, media misalignment, anti-capitalism, big tech meaning well

0:01 Jason thanks the sponsors, guests, listeners & the team for Angel Season 4! 4:38 Jason intros Menlo Ventures' Shawn Carolan 7:26 Thoughts on the market's reaction to COVID-19, when will it get back to normal? 11:51 What advice is Shawn giving to his portfolio founders? 19:07 How has the job of a VC changed with the influx of hundreds of new funds, and what impact has the large amount of dry powder done to the industry? How has Shawn adjusted his approach in response to this? 26:07 Why paying a high price on valuation for dialed in startups (like Shawn did for Uber's Series B) is still a great bet 34:13 Shawn on passing in investing on Mahalo & Jason 36:20 What was it like having a "Force of Nature" portfolio founder like Travis Kalanick, who would destroy any obstacle in his path? What are some great founder attributes? 51:24 Shawn takes us through his Siri investment 57:55 Shawn takes us through his Roku investment 1:02:25 With the influx of Seed & Series A startups, how has Shawn adjusted how he meets founders? 1:05:00 Shawn takes us through his JUMP Bikes investment, are micro-mobility unit economics broken? 1:07:43 What will the outcomes of COVID-19 be in the startup community? 1:28:05 Shawn asks Jason how to best utilize his domain expertise to create high-quality content for Menlo Ventures

0:51 Jason gives some thoughts on quarantine & intros GGV's Jeff Richards 5:11 What will this crisis look like on the other side? Benefits of having a levelheaded approach 11:38 What has Jeff seen from his seasoned portfolio founders who went through the 2008 crisis? 16:21 What advice does Jeff give to first-time founders in his portfolio? 22:22 Investor panic & differences in opinion between independent & investor board members 25:50 What could inexperienced board advice be in a time like this? 30:45 What is GGV's typical check size, how many startups do they invest in per year, and how are their funds divvied up between early-stage & growth 33:26 Chances that current deals could be renegotiated? How can founders price themselves properly? 38:05 Jeff explains liquidation preferences 42:52 How should companies approach taking venture debt in a time like this? What is Jeff's criteria for taking venture debt? 51:11 If things are going poorly, what are some things founders can do to right the ship? Examples of great pivots that saved companies 57:58 What is Airbnb's roadmap from here on out? 1:02:12 Why Jeff doesn't get enamored with IPO valuations & why he is long tech 1:08:18 Thoughts on Zoom, anti-trust laws & more

0:52 Jason intros Greylock's Sarah Guo 3:37 How did Sarah wind up at Greylock? 5:45 Sarah explains Greylock's "Zero to One" thesis & typical term commitment of a VC 11:53 How does Sarah measure her personal performance and her portfolio's performance? What are her biggest strengths as an investor? 16:12 How does she sharpen her decision-making skills? 17:53 Ranking her investment criteria: People, Markets & Product 20:26 Balancing intensity & life outside of work, the commitment of early-stage startups 27:26 Work-life balance & how the venture landscape changed over time 35:36 Greylock's structured & what was Sarah's first investment & how did it play into her investment thesis? 43:38 Sarah's investments in work-enabling software 48:00 Sarah recommends Dylan Field of Figma join the show - episode dropping Friday! 49:22 Identifying subtle flashes of brilliance in early products 58:28 Female founders being held to a higher standard 1:02:35 Anti-portfolio: Zoom 1:10:06 Sarah turns off her virtual background and reveals her location

0:53 Jason intros Bessemer's David Cowan 1:54 David explains how he got his start in Venture capital in 1992 4:22 What does Bessemer look for in a potential investor today? How has VC hiring and demographics have changed over time? 8:10 David gives an anecdote about understanding "sunk cost" 14:12 David explains how and why Bessemer started owning their anti-portfolio 16:03 Stories on passing on Facebook, Tesla, Google, PayPal, Napster & Youtube 19:13 What made Youtube standout from Napster from a regulatory perspective 24:05 David describes hearing the Twitch pitch for the first time 26:00 Consumer vs. Enterprise investing 29:42 Sales-driven culture 33:31 When is the right time to sell a company? 41:15 Anti-tech backlash... is it justified? 47:38 Who is the best Founder & CEO David has ever worked with? 52:10 Meeting Wade Foster and investing in Zapier 55:29 Are growth & product people making the best VCs today? 58:53 Thoughts on Quantum Computing 1:02:19 How is David investing in Robotics? 1:09:58 Jason ends the show by showing the trailer to David's Silicon Valley mockumentary "Bubbleproof"

0:53 Jason intros Nicole Quinn 1:59 Nicole & Jason describe their separate Calm investments, will it be the first mental health IPO? 8:00 Calm's I.C.E. celebrity engagement method & how it got them LeBron James 8:54 Investing in Sophia Amoruso & Girlboss: what is it about "Force of Nature" product people that attracts Nicole to invest? 16:03 Investing in Gwyneth Paltrow & Goop: what is Goop's business? What are the most profitable parts of their business? 19:42 Investing in Rothy's, and the inverse correlation between the success of e-commerce companies and how much they've raised 24:34 The magic moment of having shares transfer from private to public when a company IPOs 26:53 Changing her risk-averse mindset going from Wall Street to Venture Capital 33:28 Nicole's current investment interests, why voice assistants are crucial for retention 38:16 Investing in Lady Gaga & HAUS Labs: driving business via new product "drops", understanding how engaged a celebrity is in their business, celebrities as an acquisition channel 45:03 Dealing with Goop product blowback, the Netflix series & understanding the science behind it 50:12 Investing in Cameo & CEO Steven Galanis: celebrity selfie videos as a platform 54:44 What types of Founders does Nicole invest in? 56:54 How is Nicole's portfolio split up by stage?

0:51 Jason intros Bain Capital's Ajay Agarwal 3:17 Are we experiencing late-stage capitalism? Is capitalism broken? 8:22 Why is upward mobility stalling? 15:29 What is it about founders & startups that made him dedicate his life's work to? 18:46 What piece of knowledge got him in startups? Ajay describes gross margin & incremental costs 23:03 Two insights on why enterprise software is the best business 30:11 Mitt Romney at Bain Capital & issues with cultural appropriation 36:44 Ajay's early days at Trilogy Software, how software sales were different in the 1990s 42:23 Companies going from sales-driven culture to product-driven 46:52 Ajay describes one of his best investments: FourKites 49:13 Ajay describes the biggest miss of his anti-portfolio: Pinterest, and why some firms care about stage and some are stage-agnostic 54:57 Has Bain ever participated in every round of a companies life-cycle? 58:15 Effects of the SoftBank Vision Fund on venture capital as a whole