

This Week in Startups
Jason Calacanis
Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.
Episodes
Mentioned books

Feb 25, 2020 • 1h 9min
E1031: Zumper CEO & Co-Founder Anthemos Georgiades makes renting an apartment as easy as booking a hotel, shares insights on monetizing marketplaces, diversifying revenue streams to limit downside, Airbnb’s effect on the rental market & more!
0:44 Jason shares some thoughts on hard work
1:52 Jason intros Anthemos Georgiades and they discuss how Zumper was launched at TechCrunch
4:02 How did Anthemos wind up as a founder after working in consulting
6:45 What is Zumper's origin story? How many iterations did they go through before coming up with an MVP?
15:34 How did Zumper monetize their marketplace?
18:30 Partnering with Facebook & diversifying revenue
27:12 Anthemos shares thoughts on growth vs. profitability, should Brandless exist?
31:03 Uber vs. Airbnb in terms of EBITDA, thoughts on current state of Airbnb with IPO pending
37:56 Differences between Airbnb and VRBO customers according to Jason
41:00 Airbnb's effect on the rental market
46:15 Thoughts on co-living spaces
48:35 Reactions to Zumper's monthly rent report
51:20 Co-living as a business from a VC perspective
53:02 Jason gives Anthemos some NYC hotel suggestions
54:01 Jason's Hertz car rental story
59:04 Increasing difficulty of building a major team in San Francisco
1:07:38 Jason calls Ben Horowitz & answers a question from a fan

Feb 22, 2020 • 1h 26min
E1030: News Roundtable! Zapier CEO Wade Foster & Early-Stage Investor Monique Woodard on Tech Journalists vs. Founders/VCs, Twitter’s fake news detection, Kickstarter union, Blue Apron plummeting, Lambda School controversy & more!
0:36 Jason intros Monique & Wade
8:29 Tech Journalists vs. Founders/VCs
14:48 Is link-baiting press a systemic, societal issue?
19:21 Future of Founders/VCs controlling their own voice via podcasts, email newsletters, etc.
23:59 SpaceX sending passengers into space in late 2021, early 2022
28:02 Kickstarter employees vote to Unionize
41:28 Gray New World - how lucrative is the growing elderly demographic?
49:37 Twitter combatting fake/misleading news with potential new features
58:01 Blue Apron continues to plummet
1:04:13 Lambda School controversy
1:12:42 What is the path for Zapier? What is No-Code's impact on the startup industry?

Feb 19, 2020 • 2h 4min
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!
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

Feb 18, 2020 • 2h 17min
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!
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?

Feb 14, 2020 • 1h 15min
E1028: Laura Huang, author of “Edge: Turning Adversity into Advantage” shares insights on overcoming disadvantages to create an edge, being bitter vs. getting better, structural bias in tech & more
0:41 Jason intros "Edge" Author Laura Huang
3:00 How do Harvard MBA students compare with Stanford MBA students?
7:17 Why did Laura write "Edge" at this time?
8:55 Overcoming disadvantages based on race, ethnicity & gender
14:56 Laura's experience reading her own audiobook
17:23 What does her research show about structural bias against Female entrepreneurs?
23:33 How can a founder turn adversity into an advantage when asked a question with a negative bias?
28:01 How being underestimated inhibits the opportunity to enrich & provide value? What is an example of delight in p2p interaction?
36:39 How should we look at intent when discussing bias & privilege?
44:35 How to deal with being bitter vs. getting better and controlling emotions while still allowing ourselves to feel?
1:00:17 Laura & Jason share personal stories about bitter vs. better & explain how she converted her energy
1:05:09 What is Laura's hope for the lasting impact "Edge" has on its readers?

Feb 12, 2020 • 1h 30min
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
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?

Feb 11, 2020 • 1h 17min
E1027: Orreco CEO & Founder Dr. Brian Moore built a platform that optimizes performance of elite athletes, shares cutting-edge benefits of blood sampling, biomarkers, inflammation reduction, glucose monitoring & more!
0:46 Jason intros Dr. Brian Moore
3:39 What does Orreco do and how do they help elite athletes?
4:46 Do they sample blood?
6:33 What teams do they work with?
7:50 What is a bio-marker?
9:05 Why has inflammation monitoring become so popular?
15:01 Brian demos the Orreco app
22:56 What are the top reasons for elite athletes to use Orreco?
28:06 How did Brian get into this business?
30:34 How does blood differ in elite athletes? Is it regional?
36:25 What does Orreco have the biggest impact on?
43:40 What kinds of performance optimization should or shouldn't be legal in pro sports
51:12 How have they monitored machine learning?
56:47 Importance of glucose monitoring
59:15 Correlation in NBA between minutes per game and years played?
1:01:29 Taking a personal loan out to fund Orreco in the early days
1:15:39 Marc Andreessen asks Jason a question

Feb 7, 2020 • 56min
E1026: Cocoon Co-Founders Sachin Monga & Alex Cornell are building an intimate app to connect close circles, share insights on key standout features, raising money as a messaging app, breeding trust via strong domain names, ideal customers & more
0:57 Jason intros Alex & Sachin
4:46 When and why did they start Cocoon?
6:40 Why did Facebook keep changing their developer tools platform?
9:22 What is the vision for Cocoon and who is it made for?
14:58 How did they get the cocoon.com domain name and why do strong domain names breed trust?
16:57 What are they doing with customer data and how will they monetize?
20:20 Cocoon demo and Alex takes us through some key features
29:45 How difficult was raising money going up against Facebook, iMessage, etc.?
33:04 Who is their ideal customer?
38:35 Building a company in San Francisco vs. outside of it
41:57 Jason tries to invest in Cocoon live on air
47:45 Growing Cocoon in the crowded app store
51:51 Why do Cocoon founders use Notion?
54:37 Jason calls Ben Horowitz

Feb 5, 2020 • 1h 30min
E32: “Angel” podcast: Season 4 Premiere! Sarah Cannon, Partner at Index Ventures, shares insights on investing in the future of work, underrated emerging startup markets, going from the Obama Administration to Venture Capital, increasing upward mobility in America, fixing the gig economy & more!
0:01 Jason intros Season 4 of Angel & Index Ventures' Sarah Cannon
3:22 How did working for the Obama administration lead Sarah into Venture Capital?
4:56 Picking a fight with Larry Summers as an intern
15:42 Choosing Harvard's MBA program over Stanford's
18:26 Getting into VC
20:27 Working at CapitalG
24:09 How was the foundation of Index built by Danny Rimer and what is Sarah's role?
31:42 What does Index focus on during a Series A and what is a partner meeting like at Index?
36:31 Thoughts on gig economy work and is there a better way to categorize freelancers and full-time workers in the gig economy?
44:54 Sarah's proposed solution for categorizing gig economy workers
46:36 Jason's thoughts on politicians evolving their views over time
50:15 Ideas to increase upward mobility in America
1:00:35 What was Sarah's first investment? How did it work out?
1:08:42 Founders getting distracted after raising large rounds of funding
1:11:05 Thoughts on emerging international startup markets like India & Australia
1:13:19 Is France an underrated startup market?
1:17:42 What is Sarah most passionate about investing in?

Feb 4, 2020 • 1h 1min
E1025: #StartupTuneup @ Founder.University Part 2!: 6 founders pitch to Jason & Dave Samuel of Freestyle Capital on AI driving assistance, sleep-aid wearables, marijuana, B2B food analytics & more!
1:07 Megan pitches Moment AI (facial recognition software that helps drivers)
3:19 Juan pitches DreamOn (wearable and app that help you fall asleep and sleep better)
5:38 Elissa pitches Fumé (marijuana products)
7:46 Feedback & questions for Cohort 3
19:54 Rankings for Cohort 3
23:38 Stewart pitches EVOLUTIONS (marketplace for financial fitness)
25:34 Nadia pitches Keybee (marketplace for short-term rental support services)
29:21 Riana pitches Journey Foods (service that brings metrics and nutrition tools to improve product development)
31:45 Feedback & questions for Cohort 4
42:49 Rankings for Cohort 4
47:43 Jason & Dave rank the best companies from cohorts 1-4


