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This Week in Startups

Angel investor Jason Calacanis (Uber, Calm, Robinhood) interviews the world’s greatest founders, operators, investors and innovators. Get an insider’s look into venture capital, learn how to start and scale your own startup, and ride the cutting edge of technology in today’s headlines and beyond.

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E1015: Open Office Hours LIVE! Jason helps founders with their biggest challenges: gaining interest from investors, scaling while bootstrapping in a niche market, automating operations tasks, acquiring national customers & focusing on customers in the cannabis compliance space @ WSGR

0:47 Jason intros Open Office Hours 2:15 Trevor from Moovin (on-demand software to rent professional furniture) asks Jason to share some hacks on how to gain interest from investors 18:31 Jelica from Saddle Shoppe (e-commerce luxury equestrian clothing/gear) asks Jason best practices on scaling while bootstrapping in a niche market 34:49 Antonio from Youcanevent (event services marketplace) asks Jason what and how to automate operations tasks 44:44 Ossie from PICKL (B2B product/consumer data platform) asks Jason about acquiring national customers outside of California 55:57 Jontae from NatureTrak (compliance platform connecting Cannabis companies and banks) asks Jason about staying focused on different customers in a two-sided marketplace

1hr 7mins

3 Jan 2020

Rank #1

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E1005: Scale AI CEO & Co-founder Alexandr Wang creates training data for all AI applications to improve machine learning, shares insights on the future of autonomous vehicles, China’s AI advantages over US, importance of humans focusing on higher-value work & next major trends in AI

1:04 Jason intros Alexandr 2:19 Alexandr shares his personal startup history 5:17 How & why did Scale start? 8:26 What is the best example of Scale in practice? What problem are they solving? 10:44 Video demo of Scale's platform 15:34 Acquiring the scale.com domain name & insights on the unique spelling of Alexandr 17:31 How does Scale deal with data-sharing between customers? 21:34 LIDAR vs. non-LIDAR... or both? 32:29 When will we have capable self-driving vehicles from Palo Alto to San Francisco? Over/under 2030? How will gov't regulations affect self-driving? 36:03 China vs. US in the race of self-driving 41:22 Explainability in ML 47:26 Does it matter that we sometimes don't know the answer to ML systems? 51:39 Should explainability have to be proven in ML? 55:13 How should inherently biased data-sets (like US justice system) be handled via ML? 1:00:00 Importance of focusing on higher-value work 1:02:41 Are dangers of AI overblown? 1:08:50 Will "General AI" happen in our lifetime? 1:12:26 What's the next major AI trend after self-driving? 1:23:46 Does Alexandr remember a time before the Internet? 1:26:35 Jason plays "good tweet/bad tweet" with Alexandr

1hr 35mins

29 Nov 2019

Rank #2

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E967: Twilio CEO & Co-Founder Jeff Lawson on growing Twilio to 160,000 customers & a billion-dollar run rate, innovating in a trillion-dollar market, learning from Bezos, strategic timing of Twilio’s IPO, the importance of focusing on customers over competition & always waking up with a Day 1 mindset

2:14 Starting Twilio 16:54 How did Twilio 1000x revenue? 20:57 Passing $1B in revenue 31:37 Why Twilio went public when they did 41:20 What makes Jeff Bezos special?


23 Aug 2019

Rank #3

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E1014: Open Office Hours LIVE! Jason helps founders with their biggest challenges: targeting a specific segment of customers, overcoming past failures in a market, developing new nuclear energy, competing against a major incumbent & more!

0:49 Jason intros Open Office Hours Live at Neyborly 1:09 Sebastian from Tailpath asks Jason how to generate consumer habits to drive demand 18:37 Sana from Ribitt asks Jason how to overcome past failures in a lucrative market 38:21 Elizabeth from Deep Isolation talks with Jason about solving nuclear waste and developing new nuclear energy 52:12 John from Sircles asks Jason how to take on major incumbents in a large market

1hr 5mins

31 Dec 2019

Rank #4

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E977: The Next Unicorns: Standard Cognition CEO & Co-founder Jordan Fisher is making autonomous checkout available anywhere through camera computing, raised $86M to compete against Amazon Go, potential for other market opportunities, empowering both costumers and retailers — filmed at the Standard Store in SF — E3 of 10-ep miniseries

0:52 Jordan's inspiration for Standard Cognition 1:18 How Standard Cognition works 4:45 Scaling by removing friction from shopping 5:33 What kind of cameras does Standard Cognition use? 7:46 The purpose of the Standard Store 9:02 Onboarding store items to the system 13:00 Can Standard Cognition's system recognize actions? 13:45 Expanding Standard's system to other use cases 17:15 How their cameras recognize theft 22:54 Reaction to the Standard Store? 24:50 How does a store with autonomous checkout protect itself from smash & grab burglary? 29:50 Desire to adopt this technology throughout the retail industry 34:40 What autonomous checkout can do for society? 40:10 Standard Cognition is currently in "Shadow Mode", when will they officially launch in stores? 41:33 Competing against Amazon Go 46:35 How delivery plays into Standard Cognition's plan 47:05 How do big-box retailers look at the autonomous checkout movement 50:09 Reflecting on Jordan's time at the SEC


18 Sep 2019

Rank #5

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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!

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

1hr 24mins

12 May 2020

Rank #6

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E1012: Open Office Hours LIVE! Jason helps founders with their biggest challenges: goal-setting, starting a sales flywheel, converting bounced customers, capitalizing on investor feedback & more!

0:52 Kenny from Bacarai asks Jason how to start a flywheel with paid pilots as a pre-revenue company in the group airfare space 13:30 Elyse from Bloom Bras asks Jason some tactical questions around converting bounced website visitors 32:05 Pranav from Glyph asks Jason about goal-setting around raising a Seed round 50:31 Mark from Recapped asks Jason how to better understand & capitalize on investor feedback

1hr 4mins

24 Dec 2019

Rank #7

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E995: The Next Unicorns: NEXT Trucking CEO & Co-founder Lidia Yan brings trucking into the digital age with her two-sided marketplace, shares insights on finding & focusing on an untapped market, owning & innovating drayage, navigating the trucking industry as a woman & scaling the right team for success – E9 of 10-ep miniseries

0:55 Jason intros Lidia Yan 5:03 Lidia describes getting into the trucking industry and why NEXT focuses on "drayage" 13:29 How NEXT has revolutionized drayage shipping 18:22 What is a typical shipping broker's take rate 20:54 How does pricing work in the trucking industry? 27:28 How do trucking companies measure their driver's hours? 29:41 Issues within the trucking industry? 35:14 Did trucking lose employees to ride-sharing? 39:20 How NEXT compares to Uber Freight 44:50 Amazon's impact on the trucking industry 46:22 Trade war bringing inconsistency to trucking 48:41 How Lidia dealt with the challenges of being a woman starting a trucking company 50:47 Importance of getting to profitability early on

1hr 1min

30 Oct 2019

Rank #8

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E1 All-In with Chamath Palihapitiya & Jason Calacanis: US Response to COVID-19 & Impact on Startups, Venture Capital & Public Markets with David Friedberg

0:01 Jason & Chamath intro David and check in on each other's quarantines 2:26 Has the US overreacted or underreacted so far? David & Chamath give their opinions on new directives & statistics 13:15 Thoughts on potential treatment options & policy changes 22:25 Chamath explains the circumstances of recording a podcast while the Stock Market tanks in real-time 25:03 Should the US adopt Chinese & South Korean quarantine strategies? 29:53 What do the current market conditions mean for startups & VC? 41:24 Chamath explains what is currently happening in the capital markets 45:05 How close is the US on being able to do mass-testing? 54:13 Thoughts on bailouts for companies that manipulated their earnings-per-share ratio by stock buybacks? Impact on the global economy 1:03:14 Impact on luxury goods? Should there be a monthly stipend for low-income citizens? 1:12:10 COVID-19 exposing holes in the US healthcare system 1:17:44 Should we ban wet markets globally? 1:24:12 Over/Under: when Americans will be allowed to go out to restaurants again 1:28:18 When will the weekly poker game resume?

1hr 31mins

19 Mar 2020

Rank #9

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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

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

1hr 33mins

22 Nov 2019

Rank #10

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E997: HubSpot CEO & Co-founder Brian Halligan shares insights on the origin of inbound marketing, how The Grateful Dead inspired HubSpot, importance of customer experience, managing employees in the Glassdoor Era & more

0:52 Jason intros Brian Halligan 1:35 Brian describes how his job has changed as HubSpot has scaled 3:33 Jason asks Brian about buying Jerry Garcia's guitar "Wolf" 4:42 Jason & Brian reminisce over Grateful Dead shows at Giants Stadium 6:36 How the Grateful Dead pioneered "Inbound Marketing" & inspired HubSpot 15:24 How Brian met his Co-founder Dharmesh Shah 17:04 The original idea behind HubSpot 19:18 Ray Ozzie's impact on HubSpot & Brian 25:34 Benefits of introversion 30:06 Succession planning in tech 33:24 Avoiding pot-holes as CEO 35:18 Importance of customer experience in 2019 38:45 Examples of creating a great end-to-end customer experience 49:43 How Brian keeps himself sharp & motivated 52:45 Managing employees from different generations in the "Glassdoor Era"

1hr 5mins

5 Nov 2019

Rank #11