This Week in Startups

1:06 Jason intros the Pegasus concept & Yousician's Chris Thür 3:52 Chris explains Yousician 5:22 How did Yousician start and what did Guitar Hero have to do with it? 11:02 Capitalizing on Apple's inclusion of subscriptions 16:00 What were the early days of Yousician like, and was it hard to raise $? 20:32 Is being based in Finland an asset? 27:00 Chris gives his best advice for founders 29:34 Does Chris feel pressure to take $ off the table through secondary shares? 30:45 What does Chris look for in investors and what motivates Finnish employees? 34:55 Jason & Chris talk speeding tickets in Finland 42:19 Chris demos Yousician and Jason sings along 45:25 Jason tries to get on the Yousician Cap Table 47:21 Why Jason believes Yousician will get to 10 million subscribers in the next few years

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

1:08 Jason intros Andy Rachleff 2:20 Where is Wealthfront at currently? 4:44 How are traditional money managers allowed to get away with so much? 10:19 How has Andy dealt with becoming the elder statesmen at his company? 14:15 What are Wealthfront Cash Accounts? 18:27 Wealthfront's long term vision 23:49 What is high-revenue retention? How does Wealthfront maintain it? 27:44 How has Silicon Valley changed since Andy started at Benchmark? 32:10 Andy describes his greatest skill as an investor 35:30 What were the 1980's like in Venture Capital? 40:05 What do you call a VC who's never lost money? 55:01 Jason & Andy discuss how Silicon Valley is viewed in the present day

1:03 Jason's thoughts on the exploding DTC movement 4:10 How Jason discovered Eight Sleep 7:15 Jason intros Matteo Franceschetti 8:18 Matteo describes starting Eight Sleep and The Pod 15:48 What was Matteo's history before Eight Sleep 16:27 What did Matteo learn from his prior career in Solar Energy? 20:11 What has Matteo learned about users' sleep through data analysis 22:54 How does the thermo alarm work? 26:52 What is Eight Sleep doing with their sleep data? 29:36 What does the future look like for Eight Sleep? 36:50 What has Matteo learned about DTC marketing? 40:20 Dealing with returns 42:46 Which marketing channels does Matteo capitalize on? 46:30 What were Jason's instructions for reading Eight Sleep ads? 46:55 Are pop-up locations a possibility? 49:03 What is the endgame for smart-fitness products like Peloton & Tonal? 56:04 Eight Sleep's $40M raise

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

0:53 Jason intros Brian Chen 1:15 Brian demos ROOM’s collaboration with Calm 2:42 How did ROOM get their room.com domain name? 3:49 Upside & downside of open floor plans 5:52 Why ROOM manufactures the product in Indiana (for US distribution) & Portugal (for European distribution) as opposed to China 13:47 How did Brian convince VCs to invest in his DTC furniture business 18:13 What Brian thinks about ROOM’s defensibility 21:20 ROOM’s case studies with Density 26:20 How does Brian keep ROOM so capital efficient? 31:28 How does ROOM ventilate their booths? 34:58 Will ROOM raise another round or continue building off profitability? 36:49 What will ROOM’s next products be? 40:05 What would a Jason themed booth look like? 44:01 Alternative solutions for manipulating open floor plans

0:53 Jason intros Sajith Wickramasekara 1:40 What does Benchling do? 2:24 How did Sajith get into life science? 6:55 Benchling's value proposition for scientists 9:04 How do they charge? 10:43 Is Chamath Palihapitiya the most famous Sri Lankan in the US? 13:25 Why immunotherapy is the most exciting development in life science 19:00 3D Printing & harvesting organs in other species 20:50 Ethics of editing a human embryo 28:19 How did the scientific community respond to the embryo controversy 29:52 Breakthroughs in gene therapy 34:09 Defining the line between quackery & brilliance 42:37 Upside & downside of genetically modified crops 47:54 What is the best approach for breakthroughs in life science?

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"

0:58 Jason intros Alex MacCaw 2:26 What is Clearbit? 8:53 What are some Clearbit use cases? 12:48 Benefits of cashflow positivity in terms of fundraising 15:39 How Jason felt about Alex Tew’s Calm investor updates 18:59 GDPRs effect on Clearbit and the industry as a whole 27:37 How did Alex go from anti-coaching to benefitting from a CEO coach? 32:49 Alex’s experience finding a CEO coach from Naval Ravikant 34:22 What did Alex learn about company building from his coach? 38:39 Clearbit’s therapy policy 44:10 Alex’s history before Clearbit 47:16 Jason describes his first business, “Jason’s Hot Tapes” 49:37 What is Clearbit X? 53:26 Alex gives advice to his younger self

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