

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 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

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

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

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?

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

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?

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

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

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"

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


