This Week in Startups

Jason Calacanis
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Feb 4, 2020 • 45min

E1024: #StartupTuneup @ Founder.University: 6 founders pitch to Jason & Dave Samuel of Freestyle Capital on merging communication networks, athlete performance tracking, DTC women’s clothing, smart tabletop gaming systems & more!

1:31 Bryan pitches Project OWL (smart communications platform) 3:46 Erin pitches Nude Barre (DTC eco-friendly hosiery) 6:02 Mike pitches STACT (Athlete performance tracking) 8:05 Feedback & questions for Cohort 1 16:53 Rankings for Cohort 1 19:53 Jonathan pitches Move38 (smart tabletop gaming) 22:04 Brandon pitches ReplyBuy (text messaging support for sports, entertainment & higher education) 24:20 Stella pitches Stella Carakasi DTC (Size-inclusive & affordable luxury clothing for women) 28:22 Feedback & questions for Cohort 2 37:55 Rankings for Cohort 2
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Feb 1, 2020 • 1h 47min

E1023: News Roundtable! Machine Zone CEO Kristen Dumont & The Register’s Iain Thomson on Bezos phone hack, Tesla valuation skyrocketing, DJ Elon, Coronavirus, Barstool Sports funding, unions, proposed Uber/DoorDash merger & more!

0:48 Jason intros Iain Thomson & Kristen Dumont 1:58 Iain on the grim state of his WeWork office 4:34 Bezos phone hack, Saudi interference 15:12 DJ Elon plays Jason out of the break 16:45 $TSLA vs. $TSLAQ, Elon haters & more 23:07 Airborne Tesla in LA 27:30 Coronavirus effects on business, are China's numbers legit? 35:27 How regulated are food markets in China? 47:46 Iain's thoughts on Brexit 50:19 Barstool Sports, unions, do modern unions disincentivize top performers? 1:06:37 Uber/DoorDash proposed merger, is SoftBank getting desperate? 1:17:15 Leaked Column deck, founder derangement 1:28:35 France/UK big-tech tax, should Amazon pay extra? 1:34:31 Who wins the 2020 Election? 1:41:36 Jason gets Ben Horowitz on the line to end the sho
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Jan 28, 2020 • 1h 7min

E1022: One Drop CEO & Founder Jeff Dachis helps people with diabetes manage & improve their blood-sugar levels, shares insights on making data actionable, recent strategic partnership with Bayer, issues with US healthcare & potential life-expansion

0:47 Jason intros One Drop CEO Jeff Dachis 2:37 What was Jeff's original vision with One Drop? How has it evolved over time? 5:39 How did One Drop go from collecting data to making it actionable? 8:09 How important was getting the One Drop retail products into Apple stores? 9:46 Raising money as a hardware healthcare product 15:23 How did the Bayer partnership come about? 17:57 Have any major drug companies built software to manage what happens after taking medication? 21:19 What is the One Drop business today? How does coaching play into their product? 30:27 Who are One Drop's enterprise sales targets? Why don't more companies have health practitioners in-house? 36:37 Should employers be tied to healthcare? 40:04 What contributes most to the diabetes epidemic? 44:46 What are continuous glucose monitors? How do they help? 48:34 Why is insulin so expensive in the US compared to other countries? 51:47 Will we ever be able to know our blood sugar levels without intrusive hardware? 57:47 Will humans see average life-expansion into the 100's over the next few decades? 1:02:12 How gene-therapy becomes dangerous
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Jan 24, 2020 • 52min

E1021: Bubble Co-CEO & Co-Founder Emmanuel Straschnov built a no-code platform to empower the next generation of programmers, shares insights on bootstrapping to over 300k users, developing skills while scaling & more

0:53 Jason intros Bubble CEO Emmanuel Straschnov 4:25 Defining "no-code" and how Bubble differs from other no-code tools? 9:04 How much more efficient is Bubble than popular coding schools? How advanced do you have to be to learn Bubble? 14:16 Emmanuel shares Bubble's origin story and explains what Bubble unlocks for startups? 16:51 Emmanuel demos Bubble & explains notrealtwitter.com 21:17 What are some Bubble success stories? 26:12 Why did Emmanuel wait 7 years to raise their Seed Round? 29:23 Will no-code decrease the demand for developers over time? 33:26 What is Bubble making per user per year? What will that be in 5 years? 34:32 When did VCs take interest in Bubble? 39:43 How are Emmanuel's managerial skills developing as Bubble scales their team? 46:13 What is the core beachhead for Bubble? 48:11 Is there a no-code education platform in the works?
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Jan 21, 2020 • 1h 22min

E1020: CEO/Investor Coach & Author Matt Mochary shares insights on developing his coaching method, understanding & overcoming primal fear, addressing imposter syndrome & more

0:01 Calling all writers! Apply to be the first TWiST Archivist at twistarchivist.com 2:42 Jason intros CEO Coach & Author Matt Mochary 4:49 How and why did Matt decide to become a CEO coach? 8:32 What is the secret to being a great coach for investors & CEOs? 12:12 Drawing feedback out of employees 19:27 How to differentiate healthy fear from paralyzing fear? 32:06 How is Matt's method structured? 34:52 Understanding & dealing with imposter syndrome 40:27 Differences between coaching Gen-X & Millennials 42:33 Starting the Mochary foundation helping formerly incarcerated people get & keep legitimate jobs 48:19 Understanding negative motivation and transforming into purpose-filled motivation 52:39 What is Matt's "Shadow CEO" Method 54:04 What does Matt charge? 54:52 Matt coaches Jason live on air
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Jan 17, 2020 • 1h 8min

E1019: Mahmee CEO & Co-Founder Melissa Hanna is helping new moms navigate thru postpartum care, shares insights on getting Serena Williams & Mark Cuban to invest, improving the experience for mothers of color & adding structure to a fragmented industry

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?
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Jan 14, 2020 • 48min

E1018: #AskJason! Avoiding first-time founder mistakes, causes of big-tech layoffs, participating in a Series A as an Angel, running a US-based startup as an international student, importance of having a strong lead investor & more!

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
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Jan 10, 2020 • 1h 4min

E1017: Open Office Hours LIVE! Jason helps founders with their biggest challenges: scaling as a solo founder, reducing churn, raising capital in a heavily regulated field, pivoting from one-time payments to SaaS & more @ WSGR

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
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Jan 7, 2020 • 1h 39min

E1016: Substack CEO & Co-Founder Chris Best empowers writers via his email newsletter platform, shares insights on driving change in the attention economy, raising $15M from a16z, providing value to retain talent & more

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"
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Jan 3, 2020 • 1h 7min

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

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