This Week In VC: A Discussion with Jonathan Strauss

This episode of "This Week In VC" focuses on a discussion with Jonathan Strauss, a former Yahoo! executive and the founder of awe.sm. Strauss shares his insights on various tech topics, including the struggles of Yahoo!, the rise of Facebook, and the future of social media.

• The episode delves into the reasons behind Yahoo!'s downfall, exploring the company's missed opportunities and its inability to adapt to the changing landscape of the internet.
• Strauss discusses the controversial decision to appoint Marissa Mayer as Yahoo's CEO and whether Ross Levinsohn would have been a better choice to lead the company.
• The episode also explores the potential of alternative social media platforms like App.net and their challenges in competing with Facebook.

Facebook's Aggressive Strategy

The episode sheds light on the aggressive strategy employed by Facebook towards potential competitors. The discussion centers around Facebook's infamous "we can buy you or bury you" meeting with App.net, exploring the ethical and strategic implications of such tactics.

• The conversation highlights how startups need to navigate a complex landscape where giants like Facebook can exert significant influence.
• Strauss emphasizes the importance of channel strategies for startups, drawing parallels to the way traditional product companies leverage distribution networks.

The Rise of "Smart Links" and awe.sm

The episode explores the unique value proposition of awe.sm, a startup founded by Jonathan Strauss that focuses on providing "smart links" for developers.

• Strauss explains the difference between awe.sm and popular link shortening services like Bitly, emphasizing the ability of awe.sm to embed valuable data into links, enabling more effective social media campaigns.
• The conversation highlights the challenges of differentiating a startup from established market leaders during fundraising rounds.

Lessons Learned from Fundraising

Jonathan Strauss shares practical advice he gleaned from his fundraising experiences for awe.sm, emphasizing the importance of dedicated time and effort.

• Strauss underscores the importance of developing a clear narrative and value proposition to effectively communicate with investors.
• The episode discusses various venture capital strategies, including the "always be fundraising" approach.

The Future of Twitter and Open Systems

The episode concludes with Jonathan Strauss and the host expressing their belief in the potential of Twitter as an open system for social media.

• They discuss Twitter's role in fostering democratization and social disruption, emphasizing the importance of open platforms for innovation and communication.
• Strauss describes himself as a "commercially practical techno hippie," highlighting the growing trend of tech entrepreneurs who seek to combine social and commercial goals.

Facebook's Impact on the Tech Landscape

The episode underscores the significant influence that Facebook exerts on the tech landscape, highlighting the challenges and opportunities it presents for startups. The discussion explores the complexities of competing with such a powerful platform, emphasizing the need for strategic thinking and resourcefulness.

• The episode serves as a reminder that the world of venture capital is often characterized by competition and the need to navigate complex power dynamics.
• The fundraising challenges faced by startups like awe.sm, particularly those competing with established players like Bitly, demonstrate the importance of developing a unique value proposition and effectively communicating it to investors.

The Evolution of Social Media and the Rise of App.net

The episode sheds light on the evolving landscape of social media and the potential of alternative platforms like App.net to challenge the dominance of Facebook. The conversation explores the potential of social networks to foster open communication and empower users, while also acknowledging the challenges of competing with entrenched platforms.

• The discussion touches on the debate about ad-supported models in social media, highlighting the need for startups to find a balance between monetization and user experience.
• The episode provides insights into the strategies that startups can employ to differentiate themselves in a crowded market, emphasizing the importance of innovation, community building, and effective communication.

Yahoo's Struggles and the Search for a New Identity

The episode delves into the struggles of Yahoo! and its attempts to redefine its identity in a rapidly changing tech landscape. The discussion highlights the importance of adaptability and innovation in the face of fierce competition, underscoring the challenges of maintaining relevance in a market dominated by giants like Google.

• The episode serves as a cautionary tale for companies that fail to embrace change and adapt to evolving user needs.
• The conversation emphasizes the importance of strategic leadership in navigating a dynamic and competitive tech landscape.