

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

Oct 11, 2019 • 1h 2min
E986: StockX Co-founder Josh Luber is building a stock market for things, shares insights on the two cultural shifts that brought sneaker culture mainstream, attracting Mark Wahlberg, Eminem & Steve Aoki to invest along with Google Ventures & Marc Benioff & growing a unicorn out of a sneaker-data si
Josh Luber, Co-founder of StockX and a sneaker market innovator, dives deep into the explosive sneaker culture's evolution from casual wear to coveted collectibles. He shares insights on the influence of celebrities like Michael Jordan and Kanye West, and how their endorsements transformed sneaker ownership into a status symbol. Luber discusses attracting high-profile investors, the importance of authenticity in the resale market, and innovative ideas like Initial Product Offerings for sneakers, painting a vivid picture of the future of sneaker trading.

Oct 9, 2019 • 52min
E985: #AskJason! Recognizing great founders as an investor, dealing with a lack of updates, raising capital through crowdfunding, the ideal makeup of today’s founder, how Angel Investing has changed since the release of “Angel”, standing out in slow-to-adapt markets
Dive into the fine line between great founders and mediocre ones, exploring key traits like product obsession and understanding customer needs. Learn about the importance of transparent communication in angel investing, especially regarding updates. Discover the shifts in angel investing dynamics, emphasizing profitability and customer-centric approaches. Uncover how crowdfunding is evolving, inviting non-accredited investors, and the challenges of securing funding in today’s competitive landscape. Plus, tips on standing out in slow-to-adapt markets!

Oct 4, 2019 • 57min
E984: Vice Ventures Founding Partner Catharine Dockery raised $25M to invest in vices: marijuana, sextech, gambling, alcohol, vaping; shares insights on hacking her way into VC through cold emails & a strong investment thesis, capitalizing on early markets hungry for investment
Catharine Dockery, Founding Partner of Vice Ventures, discusses her pioneering venture capital firm focused on taboo industries like cannabis, sextech, and gambling. She shares her journey of raising a $25M fund and her unique investment thesis centered on harm reduction. Dockery also recounts the surprising responses she received while reaching out to investors, including Marc Andreessen. Topics like the appeal of psychedelics and the complexities of gambling investments highlight the shifting perceptions in the marketplace.

Oct 4, 2019 • 1h 1min
E983: The Next Unicorns: Zola CEO & Co-founder Shan-Lyn Ma shares insights on growing her all-in-one wedding platform in a $100bn market, adapting to changes in wedding demographics, balancing growth and profitability while keeping her team focused, raising moral standards in tech – E5 of 10-ep mini
Shan-Lyn Ma, CEO and co-founder of Zola, discusses her innovative approach to the wedding industry, highlighting the challenges of competing against giants like Amazon. She shares insights on changing wedding demographics, including the rising age of couples and evolving relationship norms. Shan also reflects on the importance of balancing growth and profitability while fostering a focused team. Additionally, she emphasizes the need for higher moral standards in tech and shares her experiences as a female founder facing underestimation in a male-dominated space.

Oct 1, 2019 • 45min
E982: Karmic Bikes Founder Hong Quan on creating the “Tesla of E-Bikes” with OSLO, bootstrapping through Kickstarter, lowering costs as a strategy, insights on U.S. resistance to widespread E-Bike adoption, & why this vehicle is the future of transportation, plus Office Hours with Jason!
In this engaging discussion, Hong Quan, CEO and co-founder of Karmic Bikes, shares insights into creating the OSLO, dubbed the 'Tesla of E-Bikes.' He delves into the various e-bike classifications and their impact on adoption in the U.S. A highlight is his unique approach to lowering costs through Kickstarter. Hong also explores barriers to e-bike popularity in America, contrasting it with Europe’s embrace of these innovative vehicles. Plus, don’t miss his surprise rap performance, adding a fun twist to the micromobility conversation!

Sep 27, 2019 • 1h 12min
E981: Roy Bahat, Head of Bloomberg Beta, shares the myths of venture capital, the great value of founders turned investors, why VCs reject startups, searing insights on fundraising & valuations, and predictions on the future of enterprise, AI, work & automation @ LAUNCH Accelerator
Roy Bahat, Head of Bloomberg Beta, brings a wealth of experience in venture capital with a focus on the future of work and machine intelligence. He debunks common myths about VC pitching and shares why angel investments from former founders hold great value. Bahat discusses critical reasons VCs reject startups and emphasizes the importance of trust in founder-investor relationships. He also explores the evolving landscape of work, the impact of automation, and highlights the need for adaptability in the face of technological change.

Sep 25, 2019 • 1h 19min
E980: The Next Unicorns: Alto Pharmacy CEO & Co-founder Mattieu Gamache-Asselin is working to fix the broken US pharmacy system by removing friction & aligning incentives among patients, doctors & insurers, shares insights on trading short-term profits for long-term success, combating the opioid cri
In this engaging conversation, Mattieu Gamache-Asselin, CEO and co-founder of Alto Pharmacy, shares his mission to transform the broken U.S. pharmacy system. He discusses unique strategies for aligning incentives between patients, doctors, and insurers. Mattieu dives into the opioid crisis, addressing accountability and ethical practices, while advocating for long-term gains over short-term profits. With anecdotes about his journey, he emphasizes operational excellence and resilience as key traits for startup founders.

Jan 1, 1970 • 1h 17min
FLASHBACK: The future of remote work, juggling APIs, and dream integrations with Wade Foster of Zapier | E2221
This Week In Startups is made possible by:Goldbelly - Goldbelly.comEvery.io - http://every.io/Zite - zite.com/twistToday’s show:Today, Zapier’s a multi-billion company helping enterprises integrate AI agents and other time-saving shortcuts into their workflows… but we had the founder on TWiST when they were just getting started!In a 2016 chat, founder Wade Foster walked JCal through their 2012 seed round, running a small entirely remote team with no HQ, the complexities of building a tool that relies on third-party APIs, and why Microsoft Office was the “Holy Grail” for his integration software.PLUS we’ve got a new entrant in your Gamma Pitch Deck competition! Tour CEO/CTO Amulya Parmer tells us how his app is saving property managers time and grief, while eliminating “looky-loos” and increasing their “hit rate.”FINALLY, Alex chats with Tomas Puig of TWiST 500 marketing analysis startup Alembic. It turns out, LLMs aren’t ideal for scrutinizing marketing campaigns because they lack the requisite historical data. Find out how they’re using Spiking Neural Networks (SNN) to dig deeper than GPT and Claude can go.Timestamps:(02:40) Amulya from Tour opens the show with praise for Jason(03:34) Tour’s 2-minute Gamma pitch: automated property tours for managers(06:47) Why Jason thinks Tour is an ideal tool for Gen Z(10:01) Goldbelly - Goldbelly ships America’s most delicious, iconic foods nationwide! Get 20% off your first order by going to Goldbelly.com and using the promo code TWiST at checkout.(13:32) How Tour can eliminate “looky-loos” and increase the “hit rate”(14:38) Why Tour prices based on individual properties and apartments(19:13) Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit every.io.(20:23) Jason wants to sprinkle some AI into Tour(24:29) Welcoming Tomas Puig from Alembic(25:12) Does epic-scale brand marketing actually pay off for these brands?(27:27) The hardest thing about being a marketer…(28:31) Alembic’s origins: organizing huge unstructured data sets(30:18) Zite - Zite is the fastest way to build business software with AI. Go to zite.com/twist to get started.(31:27) Case Study: making sense of Delta’s Olympics data(33:37) Applying simulation models and supercomputers to marketing data(35:48) How Spiking Neural Networks (SNN) help Alembic spot trends and link causal relationships(41:13) The key advantage of training models on private data(43:16) Building their own clusters vs. renting(44:41) “You don’t ask if you have Product Market Fit… You hold on for dear life.”(46:28) Flashback with Alex and Lon to Jason’s 2016 chat with Wade Foster of Zapier(54:48) The dangers of building atop other platform’s APIs(01:03:00) What Zapier learned pre-pandemic about leading remote teams(01:13:12) Why MS Office was the “Holy Grail” for early ZapierSubscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://www.twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcpFollow Lon:X: https://x.com/lonsFollow Alex:X: https://x.com/alexLinkedIn: https://www.linkedin.com/in/alexwilhelmFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisThank you to our partners:(10:01) Goldbelly - Goldbelly ships America’s most delicious, iconic foods nationwide! Get 20% off your first order by going to Goldbelly.com and using the promo code TWiST at checkout.(19:13) Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit every.io.(30:18) Zite - Zite is the fastest way to build business software with AI. Go to zite.com/twist to get started.Great TWIST interviews: Will Guidarahttps://youtu.be/pvJa2pzuXWQEoghan McCabehttps://youtu.be/9dHN4YFkgv4


