Cluely Raises $15M from a16z, $45M Modern Hacienda in the Wild | Steven Sinofsky, Anupam Singh, Miles Moen, Alexander Sen, Bryan Kim, Roy Lee, Dave Fontenot

Cluely Raises $15M from a16z, $45M Modern Hacienda in the Wild | Steven Sinofsky, Anupam Singh, Miles Moen, Alexander Sen, Bryan Kim, Roy Lee, Dave Fontenot

June 20, 2025 3 hr 44 min
🎧 Listen Now

🤖 AI Summary

Overview

This episode dives into a range of topics, from groundbreaking AI applications and investments to the evolution of technology and the challenges of scaling innovative companies. Highlights include a $15M investment in Cluely, insights from former Microsoft executive Steven Sinofsky, and discussions with leaders in AI, SaaS, and private equity.

Notable Quotes

- The most insidious distraction isn't networking or conferences—it's the second most important thing in your business. - Dave Fontenot, on the focus required for startup success.

- If you post something that deserves to go viral, it will 100% go viral. - Roy Lee, on the power of viral content in modern marketing.

- Momentum is a moat today in the era of AI applications. - Bryan Kim, on the importance of speed and distribution in AI startups.

🛠️ The Evolution of Technology and AI

- Steven Sinofsky reflects on parallels between the internet boom of the 1990s and today’s AI revolution, emphasizing how early-stage technologies often face skepticism before becoming transformative.

- He highlights the challenges of antitrust regulations during his time at Microsoft and discusses Apple's recent WWDC announcements, including their shift toward developer-friendly AI tools.

- Sinofsky also critiques the complexities of global regulatory competition, noting how regulators often compete for influence, impacting innovation.

🎮 AI at Roblox: Enhancing User Experiences

- Anupam Singh explains how Roblox uses AI for safety (e.g., chat filters) and inclusivity (real-time text translation).

- The company is pioneering generative AI for 3D content creation, allowing developers to build immersive worlds with simple text prompts.

- Singh shares staggering metrics, including 25M concurrent users and a record-breaking 16M players in a single game, showcasing Roblox's scale and growth.

💡 Cluely’s $15M Fundraise and Viral Strategy

- Roy Lee, founder of Cluely, discusses the company’s $15M Series A led by Andreessen Horowitz. The funds will be used to expand content creation and explore brain-computer interface development.

- Cluely’s desktop assistant provides real-time contextual support during meetings, with applications ranging from enterprise productivity to consumer use cases like education and dating.

- Lee emphasizes the importance of viral marketing, claiming the current content gap on platforms like TikTok creates unprecedented opportunities for growth.

🏗️ Building Startups with Focus: HF0’s Residency Model

- Dave Fontenot describes HF0 as a monastery meets hackathon, where founders strip away distractions to focus on their most critical challenges.

- The program attracts repeat founders, with 70% having built companies generating $10M+ ARR.

- Fontenot highlights success stories like OpenRouter, which scaled to trillions of tokens processed weekly by enabling seamless switching between AI models.

📊 Modernizing Legacy Industries with SaaS

- Miles Moen of Dash Fuel discusses transforming downstream oil and gas logistics by replacing outdated, paper-based systems with dynamic optimization tools.

- He explains how recent Middle East conflicts have caused significant fuel price volatility, highlighting the need for modernized systems to navigate such disruptions.

- Moen underscores the importance of balancing supply and demand to maintain stable fuel prices and industry profitability.

💼 Reinventing Private Equity with AI

- Alexander Sen, founder of Meridian, shares how his platform integrates AI to streamline deal sourcing and decision-making for private equity firms.

- Meridian combines CRM functionality with a proprietary dataset and an AI agent to identify high-potential investments, addressing inefficiencies in traditional private equity workflows.

- Sen notes the growing demand for such tools as private equity expands into areas like private credit and family offices.

AI-generated content may not be accurate or complete and should not be relied upon as a sole source of truth.

📋 Episode Description

  • (07:13) - $45M Modern Hacienda in the Wild

  • (18:11) - Timeline

  • (33:42) - Intern Tests Cluely Live

  • (01:22:29) - Steven Sinofsky, a former Microsoft executive, led the development of Windows 7 and 8 before joining Andreessen Horowitz as a board partner. In the conversation, he reflects on his career at Microsoft, discusses the impact of antitrust regulations on the company, and shares insights on the evolution of technology, including the rise of AI and its parallels to the internet boom of the 1990s. He also comments on Apple's recent developments, the challenges of recruiting AI talent, and the complexities of regulatory competition among global authorities.

  • (01:59:48) - Anupam Singh, Vice President of AI and Growth Engineering at Roblox, discusses the company's use of artificial intelligence to enhance user experiences. He highlights the implementation of automated chat filters and real-time text translation to promote inclusivity and safety, as well as the development of coding assistants powered by generative AI to streamline content creation for developers.

  • (02:30:24) - Miles Moen, CEO of Dash Fuel, a vertical SaaS company specializing in downstream oil and gas logistics, discusses the company's role in optimizing fuel delivery from producers to end consumers like gas stations and airports. He highlights the industry's reliance on outdated, paper-based systems and explains how Dash Fuel aims to modernize these processes by eliminating duplicate data entry and enhancing profit margins through dynamic optimization of fuel sourcing. Moen also addresses the impact of recent Middle East conflicts on fuel price volatility, noting significant overnight price jumps and the industry's cautious approach to potential supply disruptions.

  • (02:42:26) - Alexander Sen, founder and CEO of Meridian, a next-generation CRM platform for private equity firms, discusses his transition from nearly a decade in private equity at firms like Blackstone, Thoma Bravo, and CVC . He highlights the inefficiencies of outdated CRMs in the industry and explains how Meridian integrates AI to streamline deal sourcing and decision-making processes.

  • (02:53:04) - Bryan Kim, a partner at Andreessen Horowitz specializing in consumer and AI investments, discusses the firm's recent $15 million investment in Clulee, highlighting the company's strong distribution capabilities, innovative product that enhances user interactions through quick information access, and effective conversion of attention into revenue.

  • (03:03:54) - Roy Lee, founder of Cluli, discusses the company's recent $15 million fundraising, emphasizing plans to invest heavily in brain-computer interface development and expand their content creation capabilities. He highlights the importance of viral marketing and the potential of desktop assistants, expressing a vision to revolutionize technology and compete with industry leaders.