Jason Calacanis

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.

Be sure to visit the podcast's website and support the creator: thisweekinstartups.com

Author

Jason Calacanis

Category

Technology

Podcast website

thisweekinstartups.com

Latest episode

Oct 24, 2026

Where to listen?

Podcasts in the app Replaio Radio Coming soon

Podcasts are coming to the app soon. Install now and be the first to see a whole new take on podcasts

Get it on Google Play Install for free Android almost 10M downloads · 4.8 rating iOS soon

Episodes

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 24.01.2020

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 ar...

E1020: CEO/Investor Coach & Author Matt Mochary shares insights on developing his coaching method, understanding & overcoming primal fear, addressing imposter syndrome & more 21.01.2020

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...

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 17.01.2020

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...

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! 14.01.2020

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 foun...

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 10.01.2020

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...

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 07.01.2020

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 startup...

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 can 03.01.2020

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 J...

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! 31.12.2019

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 in...

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! 27.12.2019

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...

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! 24.12.2019

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 investo...

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 protectin 20.12.2019

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 In...

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 17.12.2019

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 Thu...

E1009: #StartupTuneup! Startmate Founders pitch Jason: AR presentation platform, experiential marketing, wearables that help menstrual cramps, education thru e-sports & more! 13.12.2019

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...

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 10.12.2019

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...

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 06.12.2019

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 Ho...

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 03.12.2019

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...

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 29.11.2019

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-...

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 a 26.11.2019

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 Doe...

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 & 22.11.2019

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 Wha...

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 ba 19.11.2019

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...

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 & 15.11.2019

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 a...

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 nex 12.11.2019

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 podc...

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 08.11.2019

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 ab...

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 & 06.11.2019

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 e...

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 05.11.2019

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...

Listen to the This Week in Startups podcast in Replaio

Radio and podcasts in one app - free, with no sign-up. Install today and do not miss the launch

Get it on Google Play

Replaio is not a podcast publisher; show names, artwork and audio belong to their authors and are distributed through public RSS feeds.