This Week in Startups - Video

Oct 17 2020 66 mins 8.7k

Jason Calacanis and a rotating group of guest experts bring you this weekly take on the best, worst, most outrageous and interesting stories from the world of Web companies. Calacanis, a podcasting pioneer, gives you an insider's look at what's happening in the tech industry with his trademark blunt style and good humor. Looking to start your own company? Need strategies for improving your business or motivating your team? Just want to catch up on what's happening in Silicon Valley and beyond? Your journey begins here.











































































E1077: “Alchemy” Author Rory Sutherland on the Darwinian approach to business, analyzing outliers, why eccentric CEOs have a psychological advantage with customers & more!
Jun 19 2020 139 mins  
1:00 Jason intros "Alchemy" author Rory Sutherland 3:45 Architecture is the cheapest way to buy art 6:01 How Rory is dealing with quarantine, why he prefers working from home, and will businesses be more efficient post-COVID? 14:12 What is Rory's job, why you should strive to create your own job title, treating the free market as Galapagos Island, using the Darwinian approach to business & analyzing outliers 19:47 Why some business successes are due to psychological discoveries: Red Bull, Dyson & Nespresso 27:25 Jason's theory on why Dyson succeeded, Kano theory on product development, why eccentric CEOs have a psychological advantage with customers, how Uber's arrival map was the key feature of the product 33:48 Why the actual value of products are typically not the proposed value of products 39:40 How new products hold value as a conversation starter, how context, setting & framing is essential to innovation 43:21 Two ways to create economic value: find something people want and figure out how to make it OR figure out what you can make and make people want it & examples: Lionfish, Fish That Ate The Whale, Royal Potatoes 50:13 Why are Americans resistant to behavioral economics? Is there still a hangover from McCarthyism? How this relates to COVID and wearing masks 1:02:08 Daily news is 95% noise, why political news coverage doesn't reflect political reality 1:11:40 Why modern politics is dumb since far left and far right are much closer than they've ever been, issues with referrals & nepotism 1:21:06 How Rory got his first job in advertising "as a weirdo" and the wildcard since he was hired as part of a group, individual hiring vs. group hiring 1:23:20 TWiST Book Club Questions - Casey: Favorite behavioral study experiment or one that he found the results to be surprising? (ie. Milgram experiment or Stanford Prison Study) 1:32:12 Catherine: What’s Rory’s favorite alchemist moment of his own from work? Has he had to advocate for an illogical idea, and how did he persuade others? 1:41:01 What will we lose by being remote? 1:51:19 Reading their own audiobooks, how cheaper and easier consumption does NOT cannibalize original mediums 2:01:26 How Rory would reinvent the theatre experience, why modern corporations are slow to innovate & experiment 2:11:18 Greatness of re-readable books and rewatchable movies/television



E1074 News: How VC can do better for underrepresented founders, Zoom shuts down Chinese pro-democracy accounts, Wall Street Bets, Reddit appoints YC CEO Michael Seibel to BoD & more with Lolita Taub & Tom Uebel
Jun 12 2020 89 mins  
0:01 Jason intros Tom Uebel & Lolita Taub 5:17 George Floyd/Black Lives Matter protests impacting Venture Capital, Angela Benton's tweets about her bad experience with Cowboy Ventures, how can VC move forward and be better towards underestimated founders? 17:37 Lolita & Jason reflect on some imperfect investor moments towards founders 23:55 How investor bias towards underrepresented founders manifests itself 28:23 Tom on focusing on diversity in hiring at the earliest stage of a companies life, how people with raw talent miss out on opportunities due to pattern-matching 39:23 Zoom's shuts down a Chinese pro-democracy account, importance of Data privacy at Command E, Jason's thoughts on Zoom only giving end-to-end encryption to paid accounts 52:36 Wall Street Bets, Meme stocks and a new generation of Robinhood traders 56:59 Reddit appoints YC CEO Michael Seibel to its board after Alexis Ohanian steps down, former interim CEO Ellen Pao has words for current CEO Steve Huffman 1:03:07 Issues of free speech & why relying solely on government organizations may be the wrong decision 1:05:45 Juneteenth observation, potential reparation ideas 1:10:27 Assessing COVID-19 recent death numbers & risk of getting back to work 1:23:03 Lolita shares her founder-investor matching tool 1:25:30 Tom demos Command E



E1072 Ask Jason: Growing as a leader, managing more experienced employees as a young CEO, Consumer SaaS pricing tips, bull markets post-COVID & more
Jun 09 2020 42 mins  
0:01 Jason teases today's questions 2:09 Luai: Is Uber still a hyper-growth company? 5:25 Weston: Advice on getting in front of/selling to startups/enterprises outside of our immediate VC network? 8:13 Martin: Do you have any resources, insights, or methods about how to get to the right price for a consumer subscription service? 12:58 Topher: What is a good shipping cadence for new code? How often should I be pushing code to production and releasing new updated versions of my app? 15:42 Delane: When you started your first business, what were your strengths/weaknesses as a manager/leader? What was young Jason like as a CEO, and how has he evolved into your current self? 19:28 Mary: In your early days, what was your leadership style towards people who were older/more experienced than you? What advice would you give a young founder for hiring older/experienced people? 20:57 Emily: If the worst of COVID has passed, what markets are you most bullish on Post-COVID? Where do you think we will see the most innovation going forward? 26:43 Danielle: What are some insights gained since taking your team fully remote? 35:15 Matt: Could you ever see an Uber/Lyft merger? What would need to take place for that to happen? 36:29 Chris: Would you rather invest in a high-growth, high-burn startup OR a moderate-growth, minimal-burn startup? 38:57 James: What software stack does LAUNCH use? Which apps are integral to your team's success and why?


E1071 Ask Jason: Black Lives Matter, Post-COVID tech hubs, Founder/VC disputes, bringing manufacturing back to the US, pre-selling SaaS products & more
Jun 05 2020 41 mins  
Jason on CNBC: https://youtu.be/V6oqvDnuAgI 0:01 Jason intros today's questions 1:51 Aaron: Thoughts on Black Lives Matter? 9:06 Joe: How can startups play a role in bringing manufacturing back to the US? 14:46 Alex: Any tips on pre-selling a SaaS product? 17:38 Arthur: How should I prepare to be a great Syndicate member in the future? In a perfect world, what does the Syndicate become? 21:13 Matthew: You often talk about founders needing to be in SV in order to be close to the action. Post-COVID, how does this change? Do places like Sydney, Vancouver, or Beijing become "big-game" cities? 28:37 Charlie: Love when you mention on your blog post a pressing need with “Someone should build this!” What’s your latest “someone should build this?” right now? 30:04 Sergey: In "Angel", you suggest to invest about $5000 per deal to minimize the risk in the beginning. Will founders care to spend an hour to pitch such a small investor? 31:26 Ruud: How common are founder/VC disputes? Is there a ranking of VCs by how founder-friendly they are? Curious if this has gotten better or worse over time? 34:48 Alex: Is it advisable to look up competitors' investors and avoid them to prevent someone at the firm from sharing critical info with your competitor? Has that happened before, or is that too paranoid? 36:35 Kirk: What is your succession plan with Launch/TWiST and why? Also, what other syndicates do you admire and why?



E1068 AMA: NEA’s Ben Narasin takes questions from founders: most important content in a pitch deck, COVID’s impact on dealmaking, traits he looks for in founders & more!
May 30 2020 48 mins  
NEA's Ben Narasin takes questions from founders: most important content in a pitch deck, COVID's impact on dealmaking, traits he looks for in founders & more! Join the TWiST Slack: https://launchevents.typeform.com/to/kLq5Bi Follow Ben: https://twitter.com/bnarasin 1:13 Paul: Has the current crisis changed your investment thesis? If so, how? 2:40 Ash/Christopher: How to overcome the money raised vs revenue generated in enterprise SaaS that requires heavy product work to reach product-market fit? 4:13 Emberlynn/Srinivas: What is the most important content in a pitch deck? 7:26 Guilherme: What will the VC funding landscape look like after the crisis passes? 8:37 Mary: What is the best way to present a newly launched startup that has been severely impacted by COVID-19 to investors? 10:48 Daniel: What advice would you offer college students passionate about venture capital so that they can also become investors? 12:22 Mark: What immediate skepticism do you have when you look at early-stage startups? 15:54 Len: What factor(s) would most set an early-stage (i.e. seed funding, launch-ready, pre-revenue) company apart from others seeking similar funding? 18:15 Aneesh: My startup sells multiple SaaS products for restaurant digitization. We don’t have the bandwidth to handle sales and marketing of all products at once. What should be our strategy to prioritize? 19:49 Linards: At what level of product traction will investors start to be interested? How does it differ across verticals? 22:40 Avidan: What role (if any) will equity crowdfunding play in the venture capital ecosystem at large? 23:43 Adam: What are you seeing related to startup valuations and VC terms post-COVID? 25:18 Emin: What kind of marketplaces would you like to see in the next 5 years? 26:34 Tammy: Do you think people will need a college degree for the jobs of the future? 28:48 Ellie: Post-WeWork, how should a tech startup with profit margins on the smaller side think about building a scalable and ultimately profitable business model? 30:15 Wei: What sectors are you investing in? What are you most excited about nowadays? 31:40 Ope: What skill sets do you need to move into VC from a non-Investment Banking background? 33:09 Suruchi/Mireille: In a medium article you wrote you wrote: "winter is here, severely ....don't obsess about the downside, think about the opportunities.” What opportunities have arisen so far? What changes are permanent and what changes are temporary? 35:20 Nghia: What are some books that you recommend today? 39:30 Ben: Are there areas that are non-investable at the moment whether it be overcrowded, overpriced, or the prospects aren’t great due to COVID? 40:24 Charles: Do you have any instances where a founder's positive or negative traits/signals have influenced a deal decision? On reflection, has instinct proved a better indicator than hard numbers? 43:42 Dave: What was your biggest exit/best investment? How did you source the deal? Alternatively, could you tell your worst anti-portfolio story (most successful company you passed on)? 44:46 Barry: What are some interesting healthcare startups or spaces that you have a favorable outlook for? 45:51 Raman: What’s your take on the future of learning?

E1067: Garry Tan, Managing Partner & Co-Founder of Initialized Capital, on dealing with downstream investors as a Seed-stage firm, software companies acting as governments, possibility of building IPO-level companies while fully-distributed & much more!
May 29 2020 97 mins  
1:03 Jason intros Garry Tan and checks in on how his quarantine has been going 4:39 How does Garry look at Initialized's portfolio companies? What are his 3 groups of companies dealing with COVID? 8:04 How will VCs react to the crisis? Why does Initialized specifically focus on Seed-stage companies? 11:13 How does Initialized contact downstream investors about their companies, and how has that changed during COVID? 14:12 Thoughts on Posterous, data-storage singularity & more 18:04 Losing thousands of photos after getting banned from Flickr and how that plays into software as the new government, becoming a super-router 22:32 How Spotify's access to public capital gives them an acquisition advantage, collab concepts 24:51 How does Initialized size their follow-on investments? 29:11 For how long is Initialized planning on operating fully remote? Thoughts on going back to work 35:56 What skills has Garry had to improve during his investing career? 43:33 How downstream investors try and take advantage of early-stage investors 47:51 Thoughts on Clubhouse investment, how/if they can scale their exclusivity 56:27 Thoughts on founders selling secondary shares, and how Chris Sacca helped Garry Tan at Posterous 1:02:09 Structural inequality leading to rich-bashing, how Fiat currency impacts welfare inequality 1:07:09 Thoughts on UBI, Instacart, potential profitability of food-delivery companies 1:11:31 Perception of Tech in the Bay Area, commercial real-estate in SF, Facebook's game-theory remote pay scale 1:18:27 Could today's tech giants (Google, Facebook, Uber) have grown to the heights they did as fully remote companies? Can IPO-level companies be consistently built while remote? 1:24:49 Do the best founders appear ageless? New Twitter features: good or bad?



E1065 AMA: Slice CEO Ilir Sela answers questions from founders: tips on selling into scattered markets (like Mom & Pop shops), COVID’s impact on the restaurant industry, scaling Slice’s $43M Series C & more!
May 21 2020 49 mins  
Slice CEO Ilir Sela answers questions from founders: tips on selling into scattered markets (like Mom & Pop shops), COVID's impact on the restaurant industry, scaling Slice's $43M Series C & more! Join the TWiST Slack: https://launchevents.typeform.com/to/kLq5Bi Check out Slice: https://slicelife.com/ Follow Ilir: https://twitter.com/IlirSela 1:05 Knyck: You mentioned Slice being a platform to provide the technology and buying power of scaled companies to small pizza businesses. Do you think that mom and pop stores in other industries like retail or services could use a similar platform, or is this type of structure specifically fitted for the economics of the pizza industry? 3:32 Michael: How do you see the restaurant industry changing in NYC post-COVID, and where do you see the growth opportunities to create a new type of offering? 5:17 Chris: I’m building a loyalty program startup for restaurants. We’re specifically targeting non-chain ethnic restaurants and customers who may have ethnic nostalgia for cultural foods. What do you think the opportunity looks like nationwide for this demographic? Are most restaurants using mainstream food ordering apps already, or is there a large segment of ethnic restaurants who are off-grid? 9:01 Graham: Mom & pops are such a scattered customer base. Can you shed some light on how you started to get momentum in the early days as a small business yourself? Did early customers have any trust issues with something as important as payment? 14:22 Laura: What is the biggest point of friction you have with adding new pizzerias to Slice? Do you experience many/any pizzerias that don't see the benefit of joining the Slice community? If so, how do you handle these? 18:50 Henry: Have you thought of doing the same for other ethnic food restaurants like Chinese, Indian, Thai etc. and what challenges do you foresee? What would be your approach to tackle? 22:04 Matt: With all the vacant retail that's about to become available, have you thought about helping pizza brands expand into ghost kitchens or helping existing pizzerias launch virtual brands (a la Chuck E Cheese)? 24:33 Ian/Andrew (similar questions): What is this funding round helping your business and platform do for the Pizza shops and their customers? How do you plan on scaling your $43M Series C? How have your plans changed since Slice has gone mostly remote? 31:10 Charles: Please expand on the apparent disparity in pricing across platforms/instore. How can food often be cheaper through a middleman? Our family often finds the most frictionless experience for our regular pizza place is to call in as it's often a single dish. How can this be simplified further? One push pizza? 37:58 Matt: Can you speak to "why pizza” and not Chinese food? At the end of the day, are you limiting yourself by picking one category? 40:32 Mahreen: Curious to know more about Slice's marketing. What marketing channels have been most effective for your platform (in acquiring both customers/new businesses)? 42:14 Ian: What response did you get from companies to sign up, was the take up easy? Or did you have to convince them in a specific sales pitch, how did you frame it? 43:51 Presh: You seem to have a curated following list on Twitter, curious to know your favorite accounts to follow that have impacted your business thinking.. top 5 accounts you recommend following? 45:31 Presh: Where does Slice need to be in order to see an IPO? 47:31 Ian: What are your plans to develop your branding and web/mobile app



E1062: News Roundtable! Acquired.FM Co-Hosts Ben Gilbert & David Rosenthal on Clubhouse’s pre-launch $100M valuation, Joe Rogan to Spotify, Uber layoffs, food delivery wars, Facebook buys GIPHY & more!
May 20 2020 117 mins  
0:31 Jason intros today's news roundtable guests Ben Gilbert & David Rosenthal 6:54 Clubhouse raises Series A from a16z at a $100M valuation pre-launch 11:12 How do $2M in secondary shares play into Clubhouse's situation? 14:08 How Clubhouse achieved "VC-Market Fit" 18:49 Was this investment worth it considering massive former outliers in the consumer social space (Facebook, Twitter, Snapchat)? Or did a16z pay too high of a price? 26:08 Bull/bear cases for founders selling secondary shares pre-launch 33:29 What impact did raising $100M for Mahalo pre-launch have on Jason? 37:18 Joe Rogan to Spotify, guess the acquisition price & macro-impact on the podcast industry 46:09 How massive is this for Spotify's position in the podcast industry? Did Apple drop the ball? 51:28 Jason to Dara: Uber should buy Dominos 52:16 How much podcast market share will Spotify have in the coming years? Will this be viewed as the landmark deal? 57:03 Uber layoffs, potential GrubHub acquisition, does the food delivery business model work? 1:04:57 Why the on-demand food delivery industry has a product-market-price fit issue, should life-long bureaucrats impact capitalist policy? 1:12:03 Who emerges victorious from the food delivery dog fight? 1:15:28 How being too reliant on one revenue stream could kill many ad-based media publications 1:24:38 Facebook's GIPHY acquisition 1:25:55 Twitter thread by GIPHY crowdfunding investor who never received their return, why Syndicate/Crowdfunding leads need to stand up for their investors to downstream firms THREAD: https://threadreaderapp.com/thread/1262574661239312384.html 1:37:20 How GIPHY's weak relationship with their DAUs led to little negotiating leverage 1:39:05 Predictions for Clubhouse's eventual business model

E1061 AMA: Hustle Fund Co-Founder & General Partner Elizabeth Yin answers 50 questions from founders!
May 19 2020 73 mins  
0:43 Prashant: Would you have benefited from an AngelList equivalent for venture capital? In other words, if up and coming venture firms can find Potential LPs in every corner of the world, instead of just SF? 1:23 Kate: What do you look for in a stand-out startup, specifically? How can I attract investors interested in what I do that will find it rewarding to invest in me besides providing raw numbers and projections? 2:50 Emin: What FOMO tactics are you using while fundraising? 4:23 Cindy: Are you open to funding sextech? How do you approach the vice clause? 5:30 Kevin: How are other seed/early-stage firms investing right now? Does Hustle Fund’s approach vary greatly from the industry standard? 6:36 Susan: How do you think about investing in blockchain, AI, spatial computing XR & AR? 7:23 Matt: At what stage should a startup calculate CAC? We are early, so my co-founder and I physically visit customers to obtain them. Eventually, we will change to a cost-effective channel. Should we put a $ value on our time and begin calculating CAC or not bother at the moment? 9:25 Saul B: How do you think about investing in the biotech/education space? Would you invest in biotech companies tackling the lack of genetics education in K-12? 10:16 Vinay: We are a startup building the graduate program search engine. We are doing what you had done in beatthegmat.com Are you still investing in this business model? 11:16 Kevin: Favorite business models to invest in these days? Conversely, least favorite business models to invest in these days? 12:36 Simeon: What would be the minimum traction for a prop-tech that you would be looking for, before investing in a startup? 12:59 Ed: What kind of trends do you see in sports tech? 13:59 Andrew: I’m an LP in Hustle Fund. How can I be a better backer? Beyond money, what can investors like me do for funds we back? 15:21 Emin: What kind of startups do you want to see in the next 5 years? 18:27 Arjun: What is too early or too late stage for Hustle Fund? Asking because we’re told our MRR $15k is too early but others say not at all. 19:05 Henry: How has your selection criteria changed for founders as a result of COVID? Are there new verticals you are backing given the circumstances? 20:07 Aaron: During this downturn, we had time to re-evaluate our approach and uncovered an exciting new path forward (with a much larger TAM). It contributes to the flywheel but is very different from our core model. How can we effectively communicate that this is the best (albeit riskier) path forward? 21:56 Gustavo: How did corona change the dynamics of raising funds in-person vs remote meetings? And do you think we’ll fully revert to old practices once things normalize? 23:23 Emin: What is your north star vision for the future of Hustle Fund? 24:51 Jason: What's the best pitch you ever got that resulted in the quickest yes and a check from you personally? How did that investment go? 26:29 Farshad: What is the nature of raising a seed round with only an MVP app in a highly regulated industry? There’s the catch 22 problem where you need a small round in order to get approval and move forward. How do investors evaluate those investments and how should you approach it as a founder? 28:05 Marten: How do you see your roadmap for approaching globally thinking, European based pre-seed/ seed startups? Many non-diluting public grants are around in the EU/Nordics which are accessible with just a small amount of private funding. 30:19 Jing: Considering different industries move/evolve at different paces: When evaluating deals, how important is this for making your investment decision? (ex: social media moved faster than e-commerce, B2C user growth is faster than B2B2C) 31:33 Timothy: How do you typically work with founders you backed?

E1060 AMA: Range CEO & Co-Founder Dan Pupius answers questions from founders: meeting & collaborating with Evan Williams, divvying up time while building a remote team, product development advice, benefits of co-founders & more
May 14 2020 38 mins  
Range CEO & Co-Founder Dan Pupius answers questions from founders: meeting & collaborating with Evan Williams, divvying up time while building a remote team, product development advice, benefits of co-founders & more Join the TWiST Slack: https://launchevents.typeform.com/to/kLq5Bi Check out Range: https://www.range.co/ Questions: 0:50 Laura: Interested in learning more about what made you want to build a company that focused on remote work? Do you personally find it challenging not to be in the same physical space as your team/the companies you work for? 2:46 Knyck: What advice would you give around developing and sticking to a product development roadmap as a first-time founder? What’s a good way to establish and calibrate sprint lengths when looking at various aspects of the build? 5:48 Henry: What are best practices around building a tight mission-driven culture when working remotely given people are not interacting face to face physically on a daily basis and focus may be impaired? 8:10 Kevin: Have you received any downstream investor interest since the start of mass quarantine across the US? Do investors see this as an opportunity? 8:57 Ciara: Can you share a little about where you want to be in 18-24 months with Range? How are you planning on scaling and what does your product roadmap look like? 10:51 Nick/Presh: How did you meet Evan Williams, what’s the story of you leaving Google for Medium, and what are some amazing insights/lessons you learned from working with him? What makes him stand out as a founder? 13:41 James: Really like the use of daily check-ins and achievement tracking within Range to keep people on track. How can we encourage these actions in important areas outside of work, where people aren't directly incentivized/forced to do so (fitness, eating, learning)? 15:52 Charles: What do you look for in a co-founder and what advice would you give to founders looking for one? Do they even need to? Also, Marmite, love it or hate it? 18:23 Lizette: What should self-funded startups be thinking about right now and 24-36 months out? 20:45 Sean: Any tips on joining a (small) tech team as a new leader? Especially fully remote? 23:24 Amanda: How did Google change in the 7 years you were there in terms of culture and product roadmap? What was it like when you joined and when you left? 25:41 Ian: How has being an Industrial designer and software developer given you insights for Range and remote working? Are you a leader or a co-founder, can you be both. 28:58 Ian: What are people expecting from a question about "culture", what are they expecting others to give them. For me, If you don't know what culture you want, you simply don't know what you want or where you are going. 32:20 Sanford: How do you split up your day starting a remote company? Do you have days when you do certain work? 34:36 Jason: What do we lose by being remote and how do we get it back if we stay remote? 37:25 Nick: You said you met Evan Williams at The Grove, what’s your go-to meal? (My favorite breakfast burrito in SF)



E1058: Slice CEO & Founder Ilir Sela helps local pizzerias compete with chains by digitizing orders & small fees, shares insights on raising $40M+ Series C during pandemic, “reverse franchise model”, viral GrubHub invoice, helping front-line workers & local pizzerias with Pizza vs. Pandemic
May 12 2020 77 mins  
0:36 Jason shares thoughts on his portfolio activity, getting back to work, leadership & more 4:20 Jason intros Slice Founder Ilir Sela 7:14 How has Slice been helping local pizzerias and front-line workers during the pandemic? https://sliceouthunger.org/pandemicpizza 9:12 What are the economics of an average privately-owned local pizzeria? How are the majority fairing during COVID-19? 13:24 What is Ilir building at Slice? What is their "reverse-franchise model" that helps local pizzerias compete with Dominos & other large chains? 15:32 What is the user-experience on Slice? 18:49 Who is Slice's average customer & how are their pizzerias handling the virus in 3 segments 29:10 Raising a $40M+ Series C during COVID pandemic & leaning on long-term relationships 32:49 Viral GrubHub invoice response - valid or overblown? Unit economics of delivery apps & how Slice's fees compare to GrubHub, DoorDash, UberEats & more 40:12 Huge delivery fees creating the need for two different menus (with higher prices on third-party platforms), how Dominos digitizing their order volume created maximum efficiency & allowed them to keep the same prices for over a decade 45:28 What is Ilir planning on doing with Slice's excess office space, how will the pandemic effect in-person work going forward? 50:10 Which groups of employees perform better under isolation? How is Slice helping employees deal with working remotely? How is New York responding to the crisis, and what will reopening look like (hybrid offices)? 1:06:53 Do business leaders have a responsibility to go through the testing process to understand how to help employees get tested efficiently?

E1057: Founders Fund General Partner Keith Rabois on stock market bounce back, domain expertise being overrated, US/China issues, 2020 election, recipe for startups success, chaos making way for a new generation of entrepreneurs & much more!
May 12 2020 84 mins  
0:56 Jason intros Keith Rabois and checks in on his quarantine, Zoom's heightened exhaustion factor & more 5:46 What will the lasting impact of COVID be on Silicon Valley & the startup funding landscape? 8:18 How the early 2000's dot-com bust paved way for a generation of new founders & why the PayPal mafia of outsiders thrived in chaos & became the establishment 14:23 What has happened to intellectual debate during COVID-19? What are first principle thinkers and why are they important to problem-solving? 20:53 Is domain expertise overrated? 22:39 Keith's on his pinned tweet about his perceived recipe for startup success 26:50 In which verticals did Keith find outliers using his low-NPS/fragmented/vertical solution strategy? 32:15 History on US relationship with China, has Trump been right on China threat, should US try and bring manufacturing back from China? 44:41 China's involvement with whistleblowers, benefits of litigation knowledge as a VC, world's reaction to China mishandling COVID info 50:40 Has Biden been soft on China? How will that play into the 2020 election? 1:00:51 Why is the stock market bouncing back so quickly with record-setting unemployment numbers? Will there be another correction? 1:03:59 What is Keith seeing across his portfolio? M&A opportunity for companies like Lyft? 1:09:34 Keith shares thoughts on the right time to go public 1:13:50 Impact of 20% unemployment on startups over the next year, mental impact of lockdown & social isolation 1:20:40 Keith's most positive outlook going forward

E1056 AMA: StartX & Nexus Events Founder Cameron Teitelman answers questions from founders: how universities with no entrepreneurial culture can mimic Stanford, building flexible & sustainable culture during COVID, scaling Nexus Events rapidly & more!
May 12 2020 36 mins  
StartX & Nexus Events Founder Cameron Teitelman answers questions from founders: how universities with no entrepreneurial culture can mimic Stanford, building flexible & sustainable culture during COVID, scaling Nexus Events rapidly & more! Join the TWiST Slack: https://launchevents.typeform.com/to/kLq5Bi Mentioned during the AMA: Cameron's new startup: https://mixer.nexusevents.io/login_mixer Cameron's most recent TWiST appearance: https://youtu.be/zsNqOLs-NVI Questions: 0:37 Cameron intros his AMA and describes his new company: Nexus Events https://mixer.nexusevents.io/login_mixer 1:31 Kevin: Are seed investors investing right now? What have StartX companies been seeing lately from early-stage investors? 2:55 James: How can universities with no entrepreneurial culture mimic the success of Stanford in creating an environment that encourages building and innovation? 4:29 James: How does the accelerator structure change for current students? What are some of the common pitfalls you have seen people make starting their company whilst finishing their degree? 7:18 Presh: Could you share more about your new startup? What are you building and why? 10:15 Ashley: How are you looking at accepting companies to StartX through the COVID lense? Which companies (in your portfolio or not) do you think are particularly well-positioned for the post COVID environment? 12:43 Jean: Regarding mentorship, in what areas do solo founders need the most help with? 14:41 Annette: Will Stanford affiliated applicants get priority over referral applicants? Would consumer startup applicants that are non-COVID related be considered during this time? 17:35 Henry: What are your thoughts in terms of building a flexible but sustainable culture? 19:26 Matt: Do you take a different approach with health tech portfolio companies and educate/manage/support them separately from the rest of the portfolio? 21:21 Laura: Given that companies don't give up equity, and there is no structured program, how do you cultivate high-level engagement with your founders/companies & mentors? 25:27 Luke: Can you talk about how the collaboration between StartX and the Stanford Hospital and Clinics works? How are the grants assessed and awarded? 26:14 Jacqui: Do you see the StartX Med COVID-19 Task Force as a new model to accelerate advances in biotech or to generate solutions for other critical global issues? 27:07 Heidi: How can other med schools around the country partner with you to develop satellite programs? 29:17 Dan: Do you have any war stories about running Nexus Events during COVID and what you’ve learned from it?


AMA 2: All Turtles CEO Phil Libin answers questions from founders: should early-stage founders prioritize data or instincts, building global products, ML risks, thoughts on remote work
May 08 2020 56 mins  
All Turtles CEO Phil Libin answers questions from founders: should early-stage founders prioritize data or instincts, building global products, ML risks, thoughts on remote work Join the TWiST Slack: https://launchevents.typeform.com/to/kLq5Bi Mentioned during the AMA: Phil's First appearance on TWiST: https://www.youtube.com/watch?v=pSYdwNHCmJA Phil presents his state machine that answers all growth questions: https://www.youtube.com/watch?v=UjyhDOb_j1I All Turtles Product Taxonomy podcast: https://www.all-turtles.com/podcast/episode-50-product-taxonomy-how-we-classify-product-pitches/ Questions: 1:03 Knyck: In your state machine model, how early should companies prioritize looking into resurrection, lines 5&9, of inactive users into low and high-value users? 2:36 David: Thoughts on Notion? I’ve been an Evernote user since ’08 but Notion seems to be winning over some Evernote fans. 3:11 Tom: 1) As CEO, what brings you the most joy as a CEO, any examples? 2) As a Software Engineer, what was one of the most difficult things you had to overcome? 3) What’s one thing early founders don’t think is as important as it really is? (Besides culture) 9:54 Graham: During the early days (pre-product market fit), do you think that more metrics are always better for founders, or would you recommend focusing on those north star metrics that can keep founders focused on the most important business levers? 12:32 Craig: How have any setbacks or failures in the past changed the way you approached problems or roadblocks. What changes will you make after COVID? 17:04 Andrii: How would you compare Notion vs Roam research vs Evernote? What are some strong and weak features of each platform? 18:26 Jeff: Have you completed your goal yet of 1 pull up? 19:36 Sina: As you said: “Many companies focus on just one market and build up from there” but you guys invest in a global presence early on in the process and tried to have users from the Asia Pacific regions from the early days. How did you guys manage to do that? Was it only marketing campaigns or did you guys have strategic partners in that region? 23:31 Tatiana: Do you consider in this matter taking some mentoring as a real addressed help? If so, I would like to take this opportunity to apply for your mentoring, if possible. What will be the best way to contact you and introduce myself? 24:39 Luke: Which products being developed at All Turtles are you most excited about? 27:59 Presh: What’s your framework for deciding which products/problems you’d like to focus on/solve at All Turtles? 30:47 Catharine: Aside from changing how you eat, what are the other two things you’ve done that have transformed your life? 32:53 Jason: Can you talk about your massive weight loss and how that did/didn’t impact you as a founder/leader? Do you think you were perceived differently based on your weight as a founder/leader? 38:02 Alex: We’re building a real-time platform called answerable and we’re wondering at what critical tipping point a platform has enough data to really derive good insights? 40:49 Alex: What would you suggest for a very regulated company (SEC) where user testimonials + referrals are either straight up not allowed or require super fine inspection to avoid being sued? 42:12 Juan Juan: I remember your story when you were planning to close down Evernote then an Angel came to your rescue writing a check that gave you the runway to success. How did that happen and what were you feeling at that time? 44:04 Vitaly: How do you estimate tech risks while investing/building a ML product? 47:08 Tammy: Will remote work actually be permanent? 48:51 Vince: After scaling Evernote and then working as a VC, I’d assume you’d advise many companies not to go the VC funding route,






AMA 1: freeCodeCamp’s Quincy Larson answers founder and developer questions
Apr 30 2020 41 mins  
freeCodeCamp Founder Quincy Larson answers questions from his exclusive AMA only on This Week in Startups' Slack! If you’d like to participate in exclusive AMAs, jam sessions, and discuss all aspects of startup life with Jason and our community of 20,000+ founders, join us at: https://launchevents.typeform.com/to/kLq5Bi Watch Quincy on E1049: https://youtu.be/OgxTDl2Z9II Follow Quincy: https://twitter.com/ossia Check out freeCodeCamp: https://www.freecodecamp.org/ Thanks to Klaviyo, Fiverr and Mint Mobile for keeping this AMA ad free! Questions: 0:33 Emin asks: What is the best tactic to build an award-winning dev team? Hire junior developers and incubate them or hire more senior people? 4:29 Rob asks: What does FCC moving to a project-based curriculum look like for someone with a moderate programming background, and where should they start approaching the freeCodeCamp curriculum? 5:41 Ilya asks: What are your thoughts on remote work for developers post COVID. What are the biggest challenges companies are facing? And how can candidates stand out in a remote job interview? 7:55 Swyx asks: What are your thoughts on SEO/building a media empire out of FCC? What about keeping FCC.org nonprofit, but making FreeCodeCamp’s YouTube and Content presence for profit? 11:06 Farjad asks: What is your advice on contributing to open-source projects like FCC and when it is appropriate/how to begin? Do I have to become an expert first? How can a beginner contribute? 13:27 James asks: Many online courses and MOOCS have high drop off rates and struggle to retain users. Have you found this with freeCodeCamp and, if so, what measures have you found work best to keep people learning? 16:40 Brady asks: What are the plans for future courses? Will there be other languages or frameworks included? 20:40 Cpulido asks: I am new to coding. I have a vision of what I want to build but I am wondering if I am being too ambitious. How do I effectively learn and build at the same time? 23:24 Jean asks: In an age of low-code and no-code, what are your thoughts on total beginners exploring a new career path today? 28:01 Luke asks: Which other founders/leaders and companies in the free code/online learning space do you think are also doing great work for the community? 30:14 Charles asks: Is there a place for those that are passionate but don't think they could ever be a great coder? Are the skills learned at FCC transferable or useful for gaining employment in another part of the tech/startup industry? 31:55 Jacqui asks: I'm curious about your experience teaching in China. What ages and subjects did you teach, and what are some differences you've seen between the education systems in the US and China and how do those differences play out into careers? 36:47 Heidi asks: As a nonprofit (public charity), what do you find is the most difficult part of soliciting donations? Is it easier to get corporations to buy into what you’re building/doing or 1:1/community to give donations?


E1050: PlayVS CEO & Founder Delane Parnell shares his incredible journey from the projects to raising almost $100M to build the esports platform of the future, breaking through as an outsider in tech, using leverage & partnerships to create a moat, his top 5 entrepreneurs & more!
Apr 28 2020 103 mins  
0:42 Jason intros PlayVS CEO & Founder Delane Parnell 2:59 What is PlayVS, how do they make money & how fast are they growing? 5:37 Attracting investors, leveraging an exclusive contract to scale across US high schools & average hours spent on the platform by players 13:26 Delane shares his backstory, from flipping shoes to owning cell phone stores in high school to getting tickets to the LAUNCH Festival in SF 26:38 How Delane turned LAUNCH Festival networking to deal flow & a job in venture capital 32:52 Meeting Peter Pham at SXSW, moving to LA to start PlayVS 38:16 Delane on his relationship with Michael Ovitz 40:20 PlayVS' go-to-market strategy & relationship with game publishers 45:51 PlayVS being co-ed & giving female gamers a safe environment to play in 51:08 Race in tech & Delane's advice on breaking into the industry as an outsider 55:57 Not taking any checks from firms who hadn't previously backed black founders 59:05 Does Darnell's intentionality about diversity create a talent advantage for PlayVS? 1:06:06 Relief of hiring high-level operators 1:11:41 LA restaurant scene discussion 1:13:39 Bird vs. Lime vs. Uber, pricing model discussion, thought on Travis Kalanick 1:23:10 Top 5 Tech entrepreneurs of all-time 1:33:40 What's going on at Airbnb?








E41: “Angel” Podcast: Shawn Carolan, Managing Partner at Menlo Ventures shares insights on his early investments in Uber, Roku, Siri & JUMP Bikes, adjusting his approach in response to hundreds of new venture funds with billions in dry powder & more!
Apr 10 2020 95 mins  
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


E1042: Balaji Srinivasan (@balajis) shares insights on Recode incident, need for decentralized citizen journalism, techlash through the years, potential COVID-19 endgames: bull, bear & base case scenarios
Apr 03 2020 112 mins  
0:55 Jason intros Balaji Srinivasan and tees up his incident with Recode's piece: “No handshakes, please”: The tech industry is terrified of the coronavirus 4:28 Balaji shares his experience with the story and his issues with corporate journalism 15:16 Balaji explains why he reacted the way he did to Shirin Ghaffary's request for an interview 19:52 History of techlash: 1995-2020, when things turned from positivity to overwhelming negativity 26:26 Balaji brings up a sentiment analysis chart published by Recode 31:25 Did both sides of the political spectrum fail in their coverage of the virus? Is citizen journalism the answer? 39:40 Balaji envisions for a new kind of journalism 41:43 Are corporate journalists too like-minded in their approach because of not being representative of the demographics of the US? 48:16 What is modern journalism's biggest blind spot? 51:22 Tips on how to start decentralizing media 54:34 Are modern journalists uncomfortable with subjects playing an active role in the reporting of the story? Did Recode & other outlets fail their readers? 1:01:55 Will the US "let it rip" strategy of dealing with COVID prove catastrophic? 1:05:53 Endgame scenarios: Bull, Bear & Base 1:10:08 Should we be experimenting with "Challenge Trials"? 1:18:52 How culpable is China for the spread of COVID-19? Should wet markets be shut down for good? 1:23:39 Why is the US still behind on mass testing? More on endgame scenarios 1:31:03 Possibility of COVID-19 being a biological weapon? 1:36:27 What should we learn from this crisis? What societal changes will happen?











E37: “Angel” Podcast: Nicole Quinn, Partner at Lightspeed shares benefits of celebrity founders like Lady Gaga & Gwyneth Paltrow, insights on investing in consumer & power of “Force of Nature” product people
Mar 11 2020 60 mins  
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?

E1035: SoftBank Managing Partner Jeff Housenbold on deploying the $100B Vision Fund, getting recruited by Masayoshi Son, counseling founders to manage massive capital, creating moats, reasons for shift toward profits, lessons from WeWork & more
Mar 10 2020 93 mins  
0:40 Jason intros Jeff Housenbold 2:16 What did Jeff do before joining the Vision Fund? How did he help scale eBay & Shutterfly? 4:15 How did he wind up at SoftBank? What was it like being recruited by Masayoshi Son? How did Masa pitch the Vision Fund to Jeff? 13:28 What was the timeframe for deploying the $100B Vision Fund? 18:10 How does SoftBank size their bets and how do they counsel founders to handle massive amounts of capital? 20:07 Coaching founders on using capital to create talent moats & build brand partnerships 22:17 Scaling their diligence alongside their capital deployment, understanding core customers & focusing on positive unit economics 28:30 How did the Uber & Didi deals go down? How close was SoftBank to investing in Lyft instead of Uber? 33:23 How SoftBank looks at investing in adjacent companies and mergers 38:42 Jeff's background & the importance of education in changing your lot in life 46:07 Changing focus from Growth to Profits, the effect of short-term thinking and its impact on Dara and Uber since their 2019 IPO 57:23 Thoughts on VTOL? Will we see VTOL vehicles or self-driving first? 1:02:16 Jeff's take on Coronavirus and its impact on the markets & how founders and CEOs can combat market volatility 1:09:38 Portfolio Review: Zume Pizza 1:11:32 Portfolio Review: Katerra 1:14:03 Jason guesses the toughest 4 industries to penetrate 1:15:03 Portfolio Review: Plenty 1:19:29 Portfolio Review: Memphis Meats 1:23:05 What happened with the WeWork investment? What % does SoftBank now own, and can they turn it around? What are some lessons learned from the entire saga? 1:27:13 Jeff shares some "Jeff-ism's of Business" 1:27:52 How is the Vision Fund II raise coming along? 1:28:36 How the scale of the Vision Fund impacts people's ability to understand their investments 1:32:05 For founders: When is the right time to engage with SoftBank?









E34: “Angel” Podcast: George Zachary, General Partner at CRV shares insights on cancer scare shifting his focus to investing in health-tech, passing on Google at MDV, CRISPR & “designer babies”, coronavirus threat, origins of Sand Hill Road & more!
Feb 19 2020 123 mins  
0:50 Jason intros CRV's George Zachary 2:20 Passing on Google at MDV and coming to peace with the anti-portfolio 5:51 Differences between leadership & management, where Steve Jobs, Larry & Sergey fell on that scale 10:27 Why 1990's VC was sales & marketing-driven instead of product-driven as it is now 12:52 What shifted the philosophy to product-driven businesses? 18:00 Meeting Elon Musk in the 1990's and backing Zip2 21:59 What were Seed investors like in the '90s? Origins of Sand Hill Road 25:48 Elon pitching Zip2 to a conglomerate of venture firms & selling Zip2 for cash 28:07 How VCs can be conceptually right and wrong in the outcome, how X.com merged with Confinity and became PayPal 33:27 Why is it harder to 3x the massive venture funds? How is age a limiting factor in VC? 40:28 "It doesn't make a difference what you pass on. It only takes 1 company to make your career." Positive & negative feedback cycles in VC. 42:54 Battling through multiple portfolio companies dying at once 44:15 What was George's biggest investment hit, both economically & personal fulfillment? 52:37 George describes his recent health scares and how they shifted his investment focus 1:04:06 Reasons the life-expectancy in the US has gone sideways in recent years 1:07:39 Potential health-tech advancements in the near future 1:21:58 Thoughts on CRISPR & "designer babies" 1:30:27 Cell-based fish & meat 1:37:32 Potential coronavirus repercussions - what's real and what's not? 1:55:13 Jason calls for eliminating handshakes


E1029: Basecamp Co-Founder & Author David Heinemeier Hansson (@DHH) debates Jason on reining in capitalism, benefits of state-run education & healthcare, big-tech disappointments, work-from-home paradigm shift, wealth tax & more!
Feb 18 2020 136 mins  
0:56 Jason intros David Heinemeier Hansson (@DHH) and asks about the work-from-home paradigm shift 5:28 Measuring programming success via budgets instead of estimates, quantifying creativity 9:57 Are incentive systems inherently bad? 13:01 How terrible commutes turned the tides for remote work in Silicon Valley, why do executives subject themselves to horrible working conditions? 17:59 What is the optimal amount of work hours per week? 19:58 Benefits of higher minimum wage 23:28 How can America "get to Denmark"? Should we rein in capitalism? 27:19 How do educational stipends work in Denmark? Benefits of state-sponsored education & healthcare 32:27 Is American bureaucracy able to change quickly? 35:52 Are gig workers being exploited? Why or why not? 45:57 Flexibility vs. Security in the gig-economy 51:20 Has the American Dream become false in America? 1:00:26 Are ISA schools (like Lambda School) an innovation or a bandaid on the failing capitalist system? 1:06:30 What do successful numbers look like for ISAs? 1:12:28 Starting Basecamp & raising from Jeff Bezos in the early days 1:19:43 Roasting Jeff Bezos on Twitter, socialism, progressivism in America 1:28:13 Amazon disappointments & how can Bezos save face? 1:36:31 Wealth tax debate 1:43:23 Which major tech companies should be broken up? 1:52:04 Will GDPR-like policies work in America? 1:55:59 What is David doing with Hey.com? Should there be two-sided consent in email read-receipt tracking? 2:03:29 Could there ever be an open-source Twitter or messaging app? Was WhatsApp it before being bought by Facebook? 2:09:34 Thoughts on tech journalism vs. big-tech 2:12:22 Can big-tech regulation fix the competitive landscape?


E33: “Angel” Podcast: Dan Rose, Chairman at Coatue Management is leading a $700M early-stage fund, shares insights on working with Bezos & Zuckerberg during pivotal years at Amazon & Facebook, 100+ angel investments, standout founder traits & more
Feb 12 2020 90 mins  
0:50 Jason intros Coatue Management's Dan Rose 1:52 Dan takes Jason through getting his internship at Amazon in 1999 and meeting Jeff Bezos 6:55 What was Amazon's core business in 1999? What was it like incubating the Kindle in the mid-2000s? 10:04 How did Bezos grow as a leader and businessman during Dan's tenure at Amazon? 18:21 How does Bezos' ability to turn Amazon around in the eyes of public investors relate to Uber, Lyft and other large & unprofitable companies? How does Bezos inspire so much loyalty? 23:27 What was Amazon's company culture during Dan's tenure? How was AWS developed? 26:08 How did Dan wind up at Facebook as employee ~130? What did he see in a young Mark Zuckerberg? 32:13 Who created the original Facebook News Feed? 35:34 How did they get the ad-network to work at scale? 42:50 Where do Elon, Bezos & Zuckerberg rank in the Pantheon of Entrepreneurs? 44:06 How did the billion-dollar acquisition offer from Yahoo! fall apart? 46:42 Why launching open registration led to the billion-dollar investment by Microsoft 48:30 Insights on the Instagram deal 51:00 How Facebook bounced back from the stock dropping from $31 to $17 shortly after IPO & how Dan's experience at Amazon helped him rally the troops? 58:44 Zuckerberg's response to mistakes 1:03:01 How did Dan wind up at Coatue Management leading a $700M early-stage fund? 1:08:01 What is Coatue's strategy around data science? 1:11:20 Dan had over 100 Angel investments before joining Coatue 1:13:18 What is Coatue's new fund strategy? 1:16:09 How does Dan think of diligence in regards to early-stage companies? 1:20:25 What does Dan want to see in an ideal founder?


















E1013: Decade Wrap-Up Roundtable! Garry Tan, Initialized Capital & Zach Coelius, Coelius Capital on the biggest hits & misses of the past decade: Trump, Theranos, Streaming, Mindfulness, Crypto, Tesla, WeWork, Amazon Prime, Vaping & more!
Dec 27 2019 66 mins  
LINKS to brackets: https://drive.google.com/open?id=1zqc-2vDRl7e86USf4okiX8DRcXPzX1HW || https://www.canva.com/design/DADuVKZjuc4/9Qt3B4m4DU-Z_HxbuDTb6w/view?utm_content=DADuVKZjuc4&utm_campaign=designshare&utm_medium=link&utm_source=sharebutton 0:29 Jason intros Garry & Zach 3:02 Jason goes over the bracket-style breakdown 3:15 Best of the decade: Ride-Sharing vs. AI/ML 8:32 Best: Amazon Prime vs. 4G LTE 10:07 Best: Tesla M3 vs. Disney buying Marvel + Star Wars IP 14:15 Best: Streaming vs. Mindfulness 17:01 Garry's Best: AI/ML vs. 4G LTE 20:20 Jason's Best: Model 3 vs. Mindfulness 24:05 Zach's Best: Ride-Sharing vs. Streaming 25:12 Jason & Guests pick their biggest win from the last decade 29:20 Jason tees up worst of the decade bracket 29:45 Worst of the decade: 2016 Election Fiasco vs. City San Francisco/Amazon Eating the World/Snowflake Culture 38:01 Worst: ICO Madness vs. Zuckerberg 40:34 Worst: WeWork vs. Vaping 44:13 Worst: Juicero vs. Theranos 44:48 Zach's Worst: 2016 Election vs. ICO Madness 45:09 Garry's Worst: Amazon Eating the World vs. ICO Madness 45:56 Jason's Worst: 2016 Election vs. Zuckerberg 49:52 Jason's Worst: WeWork vs. Theranos 51:56 Garry's Worst: Amazon Eating the World vs. Theranos 53:47 At what stage does Garry & Zach like to invest in companies? 55:52 Championship round Jason: Mindfulness vs. Zuckerberg Garry: Mindfulness vs. Theranos Zach: Streaming vs. 2016 Election Fiasco 59:52 What topics will define the 2020's?


E1011: Check Point CEO & Co-founder Gil Shwed shares insights on being the “Godfather of Cybersecurity”, growing Check Point into Israel’s most impactful tech company, pricing & developing products for an emerging market, best practices on protecting data from hackers & the next generation of cybersecurity
Dec 20 2019 61 mins  
0:48 Jason intros Gil and asks about his lengthy background in cybersecurity 3:02 What experiences inspired Check Point? 8:31 Gil explains how he raised money for Check Point in the early 1990's 14:04 How did Gil build and price his first product in a developing market? 16:46 Dealing with the first batch of cyber attacks at Check Point 19:10 What was the profile of a typical hacker in the early Internet? When did the criminality start and how does crypto tie in? 25:20 Potential of Chinese hardware hacking & hackers stealing wired money from venture firms 30:16 What are the risks associated with high-level governmental cyber security breaches 31:42 Should companies be required to build backdoors into their messaging apps? 34:24 Are Tor networks totally safe? 38:19 Gil is the "Godfather of Cybersecurity" 38:55 How protective are two-factor authentication & biometrics? 41:26 What are the most dangerous types of hacks? 44:08 Why are Microsoft products more susceptible to hacks than Apple? 46:03 Will deep-fakes lead to more threats? 50:05 Best cyber-protection advice? 55:28 Are the electrical grids a huge liability? 57:55 What is their recruiting playbook?

E1010: TWiST Live! Thumbtack CEO & Co-founder Marco Zappacosta shares insights on pivoting to optimize for consumer experience, starting a company during the great recession vs. 2019, fundraising tips & the future of Thumbtack
Dec 17 2019 70 mins  
0:52 Jason intros TWiST Live guest and one of his first investments Marco Zappacosta & Marco describes how they met in 2010 2:28 What did Thumbtack look like back in 2010? How has it changed in 2019? 6:09 Dealing with regional price differences 7:58 How much has mobile demand increased since starting Thumbtack? 11:53 What was it like running a startup in 2010 vs. 2019? 14:38 Impact of starting Thumbtack 2 weeks before Lehman Brothers went out of business 15:43 How did Marco's first try at institutional fundraising go? What did he learn from a bad investor experience? 23:13 What should founders optimize for during fundraising? 27:50 What drove growth at Thumbtack? How did they reach $10M in revenue? How did they remain focused on digging after striking oil? 31:56 Focusing on output over input 35:07 Transforming the Thumbtack experience after hitting $100M in revenue 44:33 What has Marco learned about building a marketplace over the past decade? 52:22 How has the gig-economy impacted overall employment in the US? 56:59 What is private/public healthcare's impact on entrepreneurship in a society? 1:02:33 How is Thumbtack dealing with the scarcity of trade workers? 1:04:41 What advice would Marco give himself in 2010? 1:07:16 Thoughts on minimum wage?








E1003: The Athletic CEO & Co-founder Alex Mather is building a paid online sports media publication, shares insights on attracting investors in a seemingly dying industry, managing 500+ remote writers, creating interesting angles through unique coverage & more
Nov 22 2019 93 mins  
1:05 Jason intros Alex Mather 2:08 Why did Alex launch a paid subscription publication in a seemingly dying industry? 4:32 How & where did The Athletic start? What was their thesis? 6:32 What was early feedback like from investors? 15:57 Changing approach from ad-based to subscription-based writing 21:34 Why the NHL & MLB are great for The Athletic 22:43 How do they manage young writers? 26:52 What % of their spend goes to editorial? 33:00 Managing 500+ writers 36:20 What are some ways they manage engagement? 39:08 Twitter's impact on journalism 43:39 Scouting new talent & capitalizing on layoffs 50:10 What has the inflated valuations of BuzzFeed & Vox done to the digital media industry? 55:20 How is The Athletic handling Apple's app-store subscription explosion? 58:20 Apple's impact on the boom of incredible products in our society and how The Athletic translates that to editorial 1:01:56 Alex asks Jason: "Mayor of San Francisco or owner of the Knicks?" 1:03:47 Alex shares his thoughts on the NBA/China situation 1:12:01 How does Alex go about re-activating users who have churned? 1:12:42 What does The Athletic think about the prevalence of sports gambling in America? 1:14:55 Who is the most interesting NBA player right now? 1:16:01 Jason & Alex pick who they would start an NBA franchise with today 1:17:50 Jason plays "good tweet/bad tweet" with Alex



E1000: 1000th Episode Retrospective! Jason & TWiST lifers Lon Harris, Brian Alvey, & Tyler Crowley re-live favorite moments & guests, highlighting innovations in podcasting & tech over the last decade, hitting global trends & what’s in store for the next 1000
Nov 12 2019 134 mins  
1:10 Jason intros episode 1000 + Brian Alvey & Lon Harris 3:58 "Money is the Root of All Evil" theme song 5:22 What were the first few episodes of TWiST like? 6:27 What is working with Jason like? 7:49 Tyler joins the show from Thailand and shares his history with TWiST 10:55 Brian gives his experience being the first guest on TWiST 11:59 Historic Clip: Gary Vaynerchuk on E24 18:12 History of podcasting as an industry 26:30 Historic Clip: Travis Kalanick on E180 29:54 What led to podcasting becoming a global phenomenon? 38:54 Historic Clip: Naval Ravikant on E244 42:31 How crazy was Jason in the early days of the show? 46:35 Historic Clip: Dave Goldberg on E251 47:55 Cultural shift in the general understanding of early-stage investing 53:44 Historic Clip: Chris Sacca on E291 58:36 Historic Clip: Chuck Johnson from a deleted episode 1:02:16 Historic Clip: Ed Catmull on E665/6 1:05:07 Jacqui explains how she booked Ed Catmull 1:11:24 Historic Clip: Aileen Lee on E988 1:14:52 Historic Clip: Jimmy Chamberlain on E491 1:21:43 What were "Insights from Tyler"? 1:22:47 Historic Clip: Greatest Insight from Tyler 1:25:51 Historic Clip: Peter Thiel on E525 1:27:27 Was the Peter Thiel/Gawker situation the greatest example of pettiness ever? 1:30:25 Historic Clip: Daniel Ek on E580 1:33:58 How has the perception of TWiST changed since the early days? 1:35:15 Historic Clip: Niklas Zennstrom & Sebastian Siemiatkowski on E583 1:39:57 Historic Clip: Peter Sunde on E765 1:43:23 What will the future of streaming & IP look like? 1:49:32 Historic Clip: Molly Wood on E969 1:51:05 What were the biggest changes from the last decade? 2:05:32 How has Jason changed as an interviewer? 2:09:50 Historic Clip: John Carreyrou on E828 2:11:55 Who should play Elizabeth Holmes in the upcoming movie? 2:13:02 Jason unveils the TWiST 1000 Cake and signs off and thanks everyone























E980: The Next Unicorns: Alto Pharmacy CEO & Co-founder Mattieu Gamache-Asselin is working to fix the broken US pharmacy system by removing friction & aligning incentives among patients, doctors & insurers, shares insights on trading short-term profits for long-term success, combating the opioid crisis, early days meeting Justin Kan, & innovating in a difficult market – E4 of 10-ep miniseries
Sep 25 2019 79 mins  
0:51 Jason intros Mattieu Gamache-Asselin 2:52 Changing from ScriptDash to Alto Pharmacy 4:19 Meeting and working with Twitch founder Justin Kan in the early days of Alto 6:51 Message to HBO’s Silicon Valley writing room 7:26 Working out of Justin Kan’s house 8:15 Why are pharmacies broken? How is Alto fixing them? 14:25 How did Alto’s team architect a 1.0 version of their pharmacy? 21:44 US Healthcare is broken due to bad incentive structures 28:23 Does Alto compare to Hims and Roman? 32:24 What are Alto’s profit margins? 35:00 This Week in Cinema: It’s a Wonderful Life 39:07 Maintaining balance between being scrappy/aggressive while also abiding by all medical regulations 39:54 How has Alto scaled so far? 45:55 Who is responsible for the opioid crisis? 51:24 What is Alto building to combat the crisis? 53:27 Trading short-term gain for long-term gain 56:56 How Alto was initially received among investors 1:01:03 This Week in Cinema: The Mission 1:04:30 What skill does Matt think many founders lack? 1:07:02 Operational excellence in former Amazon executives 1:13:49 #1 Lesson that Matt has learned since becoming a founder















































































































































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