

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

Dec 31, 2019 • 1h 6min
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

Dec 27, 2019 • 1h 6min
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!
LINKS to brackets: https://drive.google.com/open?id=1zqc-2vDRl7e86USf4okiX8DRcXPzX1HW
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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?

Dec 24, 2019 • 1h 5min
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

Dec 20, 2019 • 1h 1min
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 cybers
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?

Dec 17, 2019 • 1h 10min
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
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?

Dec 13, 2019 • 1h 22min
E1009: #StartupTuneup! Startmate Founders pitch Jason: AR presentation platform, experiential marketing, wearables that help menstrual cramps, education thru e-sports & more!
0:58 Jason welcomes the Startmate companies to the TWiST Studio
1:36 Zac from JigSpace pitches an AR platform for educational presentations
11:56 Teresa from Brandcrush pitches an experiential marketing platform
24:57 Jimmy from Syncio pitches a 1-click Shopify inventory sync extension
37:53 Alice from Ovira pitches a wearable device that helps stop period pain
46:14 Brett from Flaktest pitches an educational gaming platform teaching school subjects thru e-sports
54:48 Gemma from WORK180 a women-oriented job site where only endorsed employers can post jobs
1:03:34 Jason sits down with Startmate's Head of Operations Michael Batko and reveals his top 3!

Dec 10, 2019 • 1h 14min
E1008: VSCO CEO & Co-founder Joel Flory is building a photo-sharing platform free of ads, likes & comments to empower creators, shares insights on appealing to Gen Z, expanding their global reach & the magic of subscriptions
1:08 Jason intros Joel Flory
2:12 What is VSCO? How is it different than Instagram, Facebook & other photo-sharing apps?
4:33 How does VSCO grow at hyper speed without follower counts, likes, etc.?
8:28 What is VSCO's scale so far?
12:23 How does VSCO get people (mostly Gen-Z) to pay for a social network? How do they view pricing?
18:09 How VSCO uses themselves as a tool for other social networks
19:52 What is a VSCO Girl? How have they capitalized on the Gen-Z meme phenomenon?
21:31 Joel's thoughts on e-commerce
27:19 Joel is a long-time TWiST fan!
30:00 Mistakes Joel learned from in his 9-year journey at VSCO
32:26 Has iPhone photography ruined the photography industry?
36:53 How does VSCO deal with inappropriate content? How does their feed algorithm work?
43:59 Jason goes through VSCO's funding history and asks why Joel didn't sell VSCO for a massive profit
46:06 Is the greatest art created by those who don't care about what others think?
47:41 Collapse of the photography industry & sense of belonging at VSCO
51:44 Advantage of having HQ in Oakland
54:59 VSCO global expansion
57:17 Magic of subscriptions
1:05:01 The 3 truth's of VSCO

Dec 6, 2019 • 1h 5min
E1007: DoNotPay CEO & Founder Josh Browder built an AI lawyer to fight corporations & governments, demos product features & how it helps consumers, shares insights on following in footsteps of his father Bill Browder, & future of consumer empowerment
0:51 Jason intros Josh Browder & DoNotPay
2:48 Starting DoNotPay in college
6:12 How much $ has DoNotPay saved citizens since launching in 2016?
7:46 Josh explains his product roadmap to Jason
15:14 DoNotPay's mission and how Wells Fargo scammed its customers
17:37 Josh takes us through DoNotPay's suite of features starting with the robot lawyer/chatbot
19:57 Josh describes the "Skip Waiting on Hold" feature
23:37 DoNotPay's "Contract Reading AI"
28:31 Benefits of capitalist markets when consumers are treated poorly
30:51 Thoughts on Facebook?
34:05 "Hidden $ Discovery" on DoNotPay
34:47 What is DoNotPay doing for immigration
41:59 Jason asks Josh about his father, Bill Browder life and book, "Red Notice"
48:47 What is the CCPA? How does it relate to DoNotPay?
54:59 Long-term vision of DoNotPay?
56:24 Full audio of Ryan Block's call with Comcast

Dec 3, 2019 • 1h 8min
E1006: Farmer’s Fridge CEO & Founder Luke Saunders is creating a connected network of vending machines offering fresh & healthy meals, shares insights on creating a restaurant-like experience, solving food-supply chain issues, capitalizing on grassroots marketing & real-world virality & using sales
0:44 Jason intros Luke and describes how he found out about Farmer's Fridge
5:01 How did Luke overcome barriers of making a vending machine feel like a restaurant
9:18 Luke's life before Farmer's Fridge
11:52 How Luke discovered the issues of distribution that led to Farmer's Fridge
16:18 Building the first Farmer's Fridge vending machine
23:48 Ideal locations for Farmer's Fridge machines & where the first machine was placed
29:35 How did Farmer's Fridge begin to expand and hit critical mass
34:22 Using sales data to craft the most appealing menu
37:00 Getting VCs interested
41:57 Who was the first bold VC to put $ in? How did they prove themselves to institutional firms?
46:27 Machine cost over time & maximizing inventory
49:56 How hardships made Luke fearless
51:30 "Startup cannibalism"??? & low-burn culture
54:27 Farmer's Fridge NYC expansion
58:27 How does Farmer's Fridge compare to fast-casual salad restaurants

Nov 29, 2019 • 1h 35min
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


