This Week in Startups

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.

Last refreshed: June 1st, 2026 at 2:50 PM ⓘ

Follow this podcast in the Metacast mobile app to refresh it and see new episodes.

Follow on

Apple Podcasts

Spotify

RSS

Podcasts are better in Metacast mobile app

Don't just listen to podcasts. Learn from them with transcripts, summaries, and chapters for every episode. Skim, search, and bookmark insights. Learn more

Episodes

E32: “Angel” podcast: Season 4 Premiere! Sarah Cannon, Partner at Index Ventures, shares insights on investing in the future of work, underrated emerging startup markets, going from the Obama Administration to Venture Capital, increasing upward mobility in America, fixing the gig economy & more!

0:01 Jason intros Season 4 of Angel & Index Ventures' Sarah Cannon 3:22 How did working for the Obama administration lead Sarah into Venture Capital? 4:56 Picking a fight with Larry Summers as an intern 15:42 Choosing Harvard's MBA program over Stanford's 18:26 Getting into VC 20:27 Working at CapitalG 24:09 How was the foundation of Index built by Danny Rimer and what is Sarah's role? 31:42 What does Index focus on during a Series A and what is a partner meeting like at Index? 36:31 Thought...

Feb 05, 2020•1 hr 30 min

E1025: #StartupTuneup @ Founder.University Part 2!: 6 founders pitch to Jason & Dave Samuel of Freestyle Capital on AI driving assistance, sleep-aid wearables, marijuana, B2B food analytics & more!

1:07 Megan pitches Moment AI (facial recognition software that helps drivers) 3:19 Juan pitches DreamOn (wearable and app that help you fall asleep and sleep better) 5:38 Elissa pitches Fumé (marijuana products) 7:46 Feedback & questions for Cohort 3 19:54 Rankings for Cohort 3 23:38 Stewart pitches EVOLUTIONS (marketplace for financial fitness) 25:34 Nadia pitches Keybee (marketplace for short-term rental support services) 29:21 Riana pitches Journey Foods (service that brings metrics and n...

Feb 04, 2020•1 hr 1 min

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 wo...

Feb 04, 2020•45 min

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/Doo...

Feb 01, 2020•1 hr 47 min

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...

Jan 28, 2020•1 hr 7 min

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...

Jan 24, 2020•52 min

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 coachin...

Jan 21, 2020•1 hr 22 min

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 incre...

Jan 17, 2020•1 hr 8 min

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 14, 2020•48 min

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 Jas...

Jan 10, 2020•1 hr 4 min

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 Se...

Jan 07, 2020•1 hr 39 min

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 pla...

Jan 03, 2020•1 hr 7 min

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 31, 2019•1 hr 6 min

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 || 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: St...

Dec 27, 2019•1 hr 6 min

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 24, 2019•1 hr 5 min

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 hardwa...

Dec 20, 2019•1 hr 1 min

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 in...

Dec 17, 2019•1 hr 10 min

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...

Dec 13, 2019•1 hr 22 min

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 ...

Dec 10, 2019•1 hr 14 min

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 con...

Dec 06, 2019•1 hr 5 min

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...

Dec 03, 2019•1 hr 8 min

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 Sa...

Nov 29, 2019•1 hr 35 min

E1004: Yousician CEO & Co-founder Chris Thür created an interactive platform to master musical instruments, shares insights on acquiring 1M+ users, increasing retention through gamification, using profitability as leverage while attracting investors as an international startup

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 lo...

Nov 26, 2019•56 min

E1003: The Athletic CEO & Co-founder Alex Mather is building a paid online sports media publication, shares insights on attracting investors in a seemingly dying industry, managing 500+ remote writers, creating interesting angles through unique coverage & more

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 t...

Nov 22, 2019•1 hr 33 min

E1002: Wealthfront CEO & Co-founder Andy Rachleff on hitting escape velocity at Wealthfront, pioneering “self-driving money” for consumers, shares insights on product-building in 1980’s vs. today, best investor attributes, & the future of NextGen banking

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:...

Nov 19, 2019•1 hr 25 min

E1001: Eight Sleep CEO & Co-founder Matteo Franceschetti pioneered “sleep-fitness” with smart heating & cooling technology; shares insights on product iteration, delighting customers, innovating in D2C, raising $40M from LAUNCH, Founders Fund, Craft & more

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 li...

Nov 15, 2019•1 hr

E1000: 1000th Episode Retrospective! Jason & TWiST lifers Lon Harris, Brian Alvey, & Tyler Crowley re-live favorite moments & guests, highlighting innovations in podcasting & tech over the last decade, hitting global trends & what’s in store for the next 1000

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 ...

Nov 12, 2019•2 hr 15 min

E999: ROOM CEO & Co-founder Brian Chen is building phone booths for the modern office, shares insights on maximizing open floor plans, partnering with Calm to reduce stress at work, maintaining capital efficiency as a hardware startup

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 RO...

Nov 08, 2019•52 min

E998: The Next Unicorns: Benchling CEO & Co-founder Sajith Wickramasekara is increasing efficiency for scientists with a cloud-based platform, gives insights on recent life-science innovations, ethics of gene therapy & defining the line between quackery & brilliance – E10 of 10-ep miniseries

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 2...

Nov 06, 2019•55 min

E997: HubSpot CEO & Co-founder Brian Halligan shares insights on the origin of inbound marketing, how The Grateful Dead inspired HubSpot, importance of customer experience, managing employees in the Glassdoor Era & more

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 Success...

Nov 05, 2019•1 hr 6 min

← Prev Next →

Hosted on Spotify for Creators (Anchor)

For the best experience, listen in Metacast app for iOS or Android