0:58 Jason intros Melissa Hanna 1:40 What is Mahmee? What challenges are they solving for? 4:54 How does Mahmee acquire customers? Who pays for the service? 7:37 What is the current cost of having a child in the US? What are some glaring postpartum care issues in the US? 15:28 How did Melissa get Arlan Hamilton to invest? 18:42 How did Mark Cuban invest in Mahmee? 21:02 Why are black mothers 3-4x more likely to die from childbirth? Why is there such bias in healthcare? 28:31 How can Mahmee increase the birth experience across the US? 33:24 How does Melissa balance balancing the current confines in which they have to work with looking towards the future and what is possible? 38:42 What are the complexities of the healthcare space that make it hard for startups? What is the opportunity? 45:47 What are some Mahmee success stories? 51:54 Better ways to deal with postpartum depression? 57:01 How did Serena Williams come onboard via Serena Ventures?

1:39 Peter calls in and asks Jason the optimal check size if first engaging with a company in their Series A and general best practices while Angel investing 14:00 Sarah asks Jason why so many investors seek out a "lead" 17:30 Amrit calls in and asks Jason how to run a US-based startup as an international student 24:29 Jake asks Jason to identify some easily avoidable mistakes that first-time founders make 33:44 Spencer calls in and asks Jason about some of the recent layoffs in the tech space

0:46 Mehak from OnDelta (ISA School for Growth Hacking/Marketing) asks Jason best practices on scaling her business as a solo founder 10:18 Ketan from HireClub (Career coaching SaaS) asks Jason about transitioning his business to help with natural churn 20:59 Benjamin from Infection Control (Hardware infection control for sickest hospital patients) asks Jason how to raise for a medical device in a heavily regulated field 33:13 Tom from TribeXR (VR training for practical/creative skills) asks Jason how to pivot from a one-time payment to subscriptions 43:58 Corbin from LUU (Aromatherapy alternative to nicotine vapes) asks Jason how to separate his startup from JUUL and other vaping products 53:04 Thomas from Wash Day (On-demand laundry logistics app) asks Jason how to compete with large laundry incumbents as a bootstrapped startup

1:00 Jason intros Chris Best 3:24 What happened to Kik? (Chris' first startup) What did he learn from it? 5:03 What is it about email newsletters that attracted Chris? 9:41 Chris explains the AI alignment problem and how it relates to content consumption 13:58 What bad behaviors have Google & Facebook's ad algorithms created? How is Chris working to fix them? 18:09 Gamification's impact on startups 23:02 What types of writers are best suited for Substack? 29:25 How did Chris secure a $15M Series A from a16z with only 3 FTEs? Plus explaining the benefits of being "default-alive" 34:33 Are we approaching a flipping of the attention economy? 43:20 How does Substack make money? 49:46 Benefits of writer collaboration & cross-promotion 50:57 How the Deadspin situation relates to Substack 56:01 Most interesting newsletter content so far? 58:19 Dealing with offensive speech & explicit content 1:05:32 When will major publications start losing writers to Substack? 1:10:00 Plans to add audio or video? 1:11:34 What are the top-performing newsletters and what are the price ranges? 1:17:29 Ad-model vs. Paid-model at Inside & Substack 1:30:16 Chris explains the Substack fellowship 1:32:23 Thoughts on "hustle culture"

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

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

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?

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

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?

Thumbtack CEO Marco Zappacosta discusses starting a company during the great recession, fundraising tips, and optimizing the consumer experience. They also talk about the impact of the gig economy on overall employment, struggles with finding trade workers, and the debate on worker classifications.