300 episodes

Jason Calacanis and a rotating group of guest experts bring you this weekly take on the best, worst, most outrageous and interesting stories from the world of Web companies. Calacanis, a podcasting pioneer, gives you an insider's look at what's happening in the tech industry with his trademark blunt style and good humor. Looking to start your own company? Need strategies for improving your business or motivating your team? Just want to catch up on what's happening in Silicon Valley and beyond? Your journey begins here.

This Week in Startups - Video ThisWeekIn

    • Investing
    • 4.2, 230 Ratings

Jason Calacanis and a rotating group of guest experts bring you this weekly take on the best, worst, most outrageous and interesting stories from the world of Web companies. Calacanis, a podcasting pioneer, gives you an insider's look at what's happening in the tech industry with his trademark blunt style and good humor. Looking to start your own company? Need strategies for improving your business or motivating your team? Just want to catch up on what's happening in Silicon Valley and beyond? Your journey begins here.

    • video
    E1067: Garry Tan, Managing Partner & Co-Founder of Initialized Capital, on dealing with downstream investors as a Seed-stage firm, software companies acting as governments, possibility of building IPO-level companies while fully-distributed & much more!

    E1067: Garry Tan, Managing Partner & Co-Founder of Initialized Capital, on dealing with downstream investors as a Seed-stage firm, software companies acting as governments, possibility of building IPO-level companies while fully-distributed & much more!

    1:03 Jason intros Garry Tan and checks in on how his quarantine has been going

    4:39 How does Garry look at Initialized's portfolio companies? What are his 3 groups of companies dealing with COVID?

    8:04 How will VCs react to the crisis? Why does Initialized specifically focus on Seed-stage companies?

    11:13 How does Initialized contact downstream investors about their companies, and how has that changed during COVID?

    14:12 Thoughts on Posterous, data-storage singularity & more

    18:04 Losing thousands of photos after getting banned from Flickr and how that plays into software as the new government, becoming a super-router

    22:32 How Spotify's access to public capital gives them an acquisition advantage, collab concepts

    24:51 How does Initialized size their follow-on investments?

    29:11 For how long is Initialized planning on operating fully remote? Thoughts on going back to work

    35:56 What skills has Garry had to improve during his investing career?

    43:33 How downstream investors try and take advantage of early-stage investors

    47:51 Thoughts on Clubhouse investment, how/if they can scale their exclusivity

    56:27 Thoughts on founders selling secondary shares, and how Chris Sacca helped Garry Tan at Posterous

    1:02:09 Structural inequality leading to rich-bashing, how Fiat currency impacts welfare inequality

    1:07:09 Thoughts on UBI, Instacart, potential profitability of food-delivery companies

    1:11:31 Perception of Tech in the Bay Area, commercial real-estate in SF, Facebook's game-theory remote pay scale

    1:18:27 Could today's tech giants (Google, Facebook, Uber) have grown to the heights they did as fully remote companies? Can IPO-level companies be consistently built while remote?

    1:24:49 Do the best founders appear ageless? New Twitter features: good or bad?

    • 1 hr 37 min
    • video
    E1066: The Power of Accelerators E6 David Brown, CEO & Co-Founder of TechStars on leading the virtual accelerator trend, benefits of going global, sustained vs. temporary changes from COVID & more!

    E1066: The Power of Accelerators E6 David Brown, CEO & Co-Founder of TechStars on leading the virtual accelerator trend, benefits of going global, sustained vs. temporary changes from COVID & more!

    0:43 Jason intros TechStars CEO David Brown

    4:47 TechStars leading the virtual accelerator trend

    10:21 Will TechStars go with a hybrid model going forward and what key points should remote accelerators focus on?

    15:27 How did TechStars settle on the number of 10 companies per cohort?

    17:28 What has TechStars seen across their portfolio since COVID started?

    21:21 Sustained changes vs. temporary changes due to COVID, will COVID lead to more entrepreneurs?

    31:58 How to explain edge-case funding scenarios to founders who have real businesses that are having troubling raising capital, taking a long-term view on accelerator engagement, why B2B is easier than B2C

    36:22 Why angels invest in one company over the other? Do metrics matter as much as personal relationships? What are ideal founder characteristics that David looks for?

    40:25 How TechStars selects mentors by surveying their mentees, comparison against Y Combinator

    51:45 Opportunity for going global, David's relationship with Co-Founder David Cohen

    1:00:30 Would TechStars ever go public?

    • 1 hr 7 min
    • video
    E1065 AMA: Slice CEO Ilir Sela answers questions from founders: tips on selling into scattered markets (like Mom & Pop shops), COVID’s impact on the restaurant industry, scaling Slice’s $43M Series C & more!

    E1065 AMA: Slice CEO Ilir Sela answers questions from founders: tips on selling into scattered markets (like Mom & Pop shops), COVID’s impact on the restaurant industry, scaling Slice’s $43M Series C & more!

    Slice CEO Ilir Sela answers questions from founders: tips on selling into scattered markets (like Mom & Pop shops), COVID's impact on the restaurant industry, scaling Slice's $43M Series C & more!



    Join the TWiST Slack: https://launchevents.typeform.com/to/kLq5Bi



    Check out Slice: https://slicelife.com/



    Follow Ilir: https://twitter.com/IlirSela



    1:05 Knyck: You mentioned Slice being a platform to provide the technology and buying power of scaled companies to small pizza businesses. Do you think that mom and pop stores in other industries like retail or services could use a similar platform, or is this type of structure specifically fitted for the economics of the pizza industry?



    3:32 Michael: How do you see the restaurant industry changing in NYC post-COVID, and where do you see the growth opportunities to create a new type of offering?



    5:17 Chris: I’m building a loyalty program startup for restaurants. We’re specifically targeting non-chain ethnic restaurants and customers who may have ethnic nostalgia for cultural foods. What do you think the opportunity looks like nationwide for this demographic? Are most restaurants using mainstream food ordering apps already, or is there a large segment of ethnic restaurants who are off-grid?



    9:01 Graham: Mom & pops are such a scattered customer base. Can you shed some light on how you started to get momentum in the early days as a small business yourself? Did early customers have any trust issues with something as important as payment?



    14:22 Laura: What is the biggest point of friction you have with adding new pizzerias to Slice? Do you experience many/any pizzerias that don't see the benefit of joining the Slice community? If so, how do you handle these?



    18:50 Henry: Have you thought of doing the same for other ethnic food restaurants like Chinese, Indian, Thai etc. and what challenges do you foresee? What would be your approach to tackle?



    22:04 Matt: With all the vacant retail that's about to become available, have you thought about helping pizza brands expand into ghost kitchens or helping existing pizzerias launch virtual brands (a la Chuck E Cheese)?



    24:33 Ian/Andrew (similar questions): What is this funding round helping your business and platform do for the Pizza shops and their customers? How do you plan on scaling your $43M Series C? How have your plans changed since Slice has gone mostly remote?



    31:10 Charles: Please expand on the apparent disparity in pricing across platforms/instore. How can food often be cheaper through a middleman? Our family often finds the most frictionless experience for our regular pizza place is to call in as it's often a single dish. How can this be simplified further? One push pizza?



    37:58 Matt: Can you speak to "why pizza” and not Chinese food? At the end of the day, are you limiting yourself by picking one category?



    40:32 Mahreen: Curious to know more about Slice's marketing. What marketing channels have been most effective for your platform (in acquiring both customers/new businesses)?



    42:14 Ian: What response did you get from companies to sign up, was the take up easy? Or did you have to convince them in a specific sales pitch, how did you frame it?



    43:51 Presh: You seem to have a curated following list on Twitter, curious to know your favorite accounts to follow that have impacted your business thinking.. top 5 accounts you recommend following?



    45:31 Presh: Where does Slice need to be in order to see an IPO?



    47:31 Ian: What are your plans to develop your branding and web/mobile app

    • 49 min
    • video
    E1064: News Roundtable! Sam Parr & Zach Coelius on Barstool Sports vs. Call Her Daddy, SoftBank’s $17B loss, TikTok poaches former Disney exec as CEO, Facebook launches Shops & more!

    E1064: News Roundtable! Sam Parr & Zach Coelius on Barstool Sports vs. Call Her Daddy, SoftBank’s $17B loss, TikTok poaches former Disney exec as CEO, Facebook launches Shops & more!

    0:51 Jason intros Zach Coelius & Sam Parr

    2:28 Barstool Sports vs. Call Her Daddy

    6:49 Penn National Gaming stock soaring, Dave Portnoy winning this controversy

    13:17 SoftBank reports $17.7B annual loss, worst figures in 39-year history

    17:19 Does SoftBank's involvement typically include a loss of focus for the founder?

    21:43 TikTok’s parent co. Bytedance trades at a $140B valuation, poaches Disney’s former Head of Streaming as new CEO of TikTok

    25:08 Was Kevin Mayer wrong to take this role? Are TikTok's recommendation algorithms the best in the world?

    28:52 How do Chinese companies grow so rapidly?

    32:06 Facebook launches Shops, is Zuck trying to kill e-commerce giants? Zach on his experience with Facebook slowly killing his business

    40:06 How does Facebook's product organization work?

    47:13 Jason on the future of social networks

    49:56 Amazon potentially acquiring AMC Theatres, could this be an Amazon Prime upsell?

    53:52 Everyone gives their best idea for Amazon's first move after buying AMC

    59:59 Zach on his quarantine deal flow

    • 1 hr 2 min
    • video
    E1063: The Power of Accelerators E5 Joshua Baer, CEO & Founder of Capital Factory shares lessons from investing in 400+ startups, best practices for transitioning accelerators to remote, insights on SXSW cancellation & more

    E1063: The Power of Accelerators E5 Joshua Baer, CEO & Founder of Capital Factory shares lessons from investing in 400+ startups, best practices for transitioning accelerators to remote, insights on SXSW cancellation & more

    0:35 Jason intros Capital Factory CEO & Founder Josh Baer

    1:47 What is Capital Factory in its current iteration? How are they transitioning to remote? Loss of serendipity of random in-person connections

    5:38 Josh takes Jason through the SXSW cancellation

    10:29 Issues conceptualizing COVID's impact

    15:35 Transitioning to rolling cohorts & optimizing their Slack community

    21:36 Capital Factory's standard deal terms, why founders join, how returns are divvied up

    27:30 Starting Capital Factory during the last economic downturn, how millennials will react to this crisis

    30:45 Josh describes his 5 buckets of how companies are weathering the COVID storm

    35:09 Remote work's effect on startup collaboration

    41:01 COVID's effect on children, getting back to work

    47:37 What investing mistakes has Josh made, and how has he learned from them?

    56:00 What founder traits does Josh look for?

    59:14 Moving to Austin, SXSW history

    • 1 hr 11 min
    • video
    E1062: News Roundtable! Acquired.FM Co-Hosts Ben Gilbert & David Rosenthal on Clubhouse’s pre-launch $100M valuation, Joe Rogan to Spotify, Uber layoffs, food delivery wars, Facebook buys GIPHY & more!

    E1062: News Roundtable! Acquired.FM Co-Hosts Ben Gilbert & David Rosenthal on Clubhouse’s pre-launch $100M valuation, Joe Rogan to Spotify, Uber layoffs, food delivery wars, Facebook buys GIPHY & more!

    0:31 Jason intros today's news roundtable guests Ben Gilbert & David Rosenthal

    6:54 Clubhouse raises Series A from a16z at a $100M valuation pre-launch

    11:12 How do $2M in secondary shares play into Clubhouse's situation?

    14:08 How Clubhouse achieved "VC-Market Fit"

    18:49 Was this investment worth it considering massive former outliers in the consumer social space (Facebook, Twitter, Snapchat)? Or did a16z pay too high of a price?

    26:08 Bull/bear cases for founders selling secondary shares pre-launch

    33:29 What impact did raising $100M for Mahalo pre-launch have on Jason?

    37:18 Joe Rogan to Spotify, guess the acquisition price & macro-impact on the podcast industry

    46:09 How massive is this for Spotify's position in the podcast industry? Did Apple drop the ball?

    51:28 Jason to Dara: Uber should buy Dominos

    52:16 How much podcast market share will Spotify have in the coming years? Will this be viewed as the landmark deal?

    57:03 Uber layoffs, potential GrubHub acquisition, does the food delivery business model work?

    1:04:57 Why the on-demand food delivery industry has a product-market-price fit issue, should life-long bureaucrats impact capitalist policy?

    1:12:03 Who emerges victorious from the food delivery dog fight?

    1:15:28 How being too reliant on one revenue stream could kill many ad-based media publications

    1:24:38 Facebook's GIPHY acquisition

    1:25:55 Twitter thread by GIPHY crowdfunding investor who never received their return, why Syndicate/Crowdfunding leads need to stand up for their investors to downstream firms

    THREAD: https://threadreaderapp.com/thread/1262574661239312384.html

    1:37:20 How GIPHY's weak relationship with their DAUs led to little negotiating leverage

    1:39:05 Predictions for Clubhouse's eventual business model

    • 1 hr 57 min

Customer Reviews

4.2 out of 5
230 Ratings

230 Ratings

kimbi2965 ,

The best information for founders and investors

This show is not telling what to think as much as it is telling you how to think. Jason is excellant at taking you inside the heads of investors and founders to help everyone understand the startup landscape -- he is so very good at teaching you how to not be stupid and develop your insights in how to move forward.

Jurell Tanksley ,

This Week in Startups is the pulse of the tech world during the pandemic

Jason and the twist team are keeping the pipeline full of the best CEO's, giving us hope and insignt on how to adapt our businesses to a post-pandemic market. Jason and Team, TWIST is an inspiration to us all; I love the slack channel community and the concistent message to have hope, work hard, adapt and win.

Thanks Twist Team.

Clarisse Gomez ,

Awesome Podcast!!!

Jason, host of This Week in Startups podcast, highlights all aspects of business, investing and more in this can’t miss podcast! The host and expert guests offer insightful advice and information that is helpful to anyone that listens!

Top Podcasts In Investing

Listeners Also Subscribed To