This Week in Startups

Jason Calacanis
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Oct 15, 2019 • 54min

E988: Aileen Lee, Founder & Managing Partner of Cowboy Ventures, pioneered actionable change to diversify tech & VC, shares early days innovating in e-commerce, insights on current funding landscape, dangers of prioritized growth over sustainability, & lessons learned from backing winners like Dolla

Aileen Lee, Founder and Managing Partner of Cowboy Ventures, has been a trailblazer in diversifying tech and VC. In this discussion, she shares her experiences confronting early gender bias in math and her journey from GAP to Silicon Valley. Aileen dives into the skewed funding landscape, highlighting the dangers of prioritizing growth over sustainability, particularly using WeWork as a case study. She offers insights from her investment in Dollar Shave Club and emphasizes the importance of diversity in the tech ecosystem, urging for stronger inclusion initiatives.
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Oct 12, 2019 • 56min

E987: The Next Unicorns: Upgrade CEO & Co-founder Renaud Laplanche is empowering users to better understand credit through his consumer credit platform, announces the Upgrade Card, shares insights on taking LendingClub public & how startups have changed since he started his first company in 2000 – E

Renaud Laplanche, CEO and co-founder of Upgrade, previously founded LendingClub and is now revolutionizing consumer credit. He shares insights on the transition from LendingClub to Upgrade and critiques outdated credit scoring methods. The innovative Upgrade Card aims for responsible credit use. Renaud discusses the evolution of startups since 2000 and reflects on the lending landscape's challenges. He also explores the role of cryptocurrencies and emphasizes the importance of transparency in consumer finance.
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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.
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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!
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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.
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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.
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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!
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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.
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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.

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