In the 32nd episode of Cartoon Avatars former Twitter CEO Dick Costolo discusses his time at Second City with greats like Tina Fey, Amy Poehler, and Steve Carrell, successfully managing and running Twitter as a non-founder, and trying to buy Instagram. (0:00) Intro (0:58) Mark Cuban canceled (4:08) The editing room (6:07) Logan’s engagement (9:22) Welcome Dick Costolo (13:54) Dick’s time at Second City (28:16) After Second City (32:44) Why Twitter is a unique challenge (35:06) Treating all Twitter accounts equally (40:09) Social Media Regulation (42:06) Twitter monetization (44:06) Trying to buy Instagram (48:37) Social media platform Saturn (52:01) Expectation setting (57:10) Leading a company you didn’t found (59:53) Role vs identity (1:02:15) Bill Campbell’s mentorship (1:07:57) Letting people go (1:12:47) Successful managing (1:15:42) Marxist vs Darwinian management (1:19:13) Assume best intentions (1:24:40) Getting unfollowed by Elon Musk (1:30:31) Rapid fire (1:35:14) Outro  Mixed and edited: Justin Hrabovsky Produced: Andrew Nadeau and Rashad Assir Executive Producer: Josh Machiz Music: Griff Lawson  

EP 32: Former Twitter CEO Dick Costolo Talks About His Time at Second City, Running Twitter, and Missing Out on Instagram

Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.

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Steve Kaufer led Tripadvisor to multi-billion dollar success over a 20+ year run as CEO. He discusses getting acquired and spun out from IAC, becoming a public company CEO, and his biggest operating lessons from his decades-long journey. Steve also shares behind-the-scenes of his new venture, Give Freely, and reflects on his entrepreneurial path.   (00:00) Intro (01:00)  Steve Kaufer's Journey with Tripadvisor (03:18) Handling Negative Reviews and Legal Issues (05:24) Psychology of Reviews and User Behavior (10:01) Impact of AI on Review Platforms (15:02) Graduation Speech and Key Lessons (16:33) Speed Wins: The Importance of Agility (22:46) Measuring Success and Embracing Change (28:40) Hard Work and Personal Growth (36:20) Management and Leadership Insights (40:23) Setting Company Culture (48:00) Adapting to Market Changes (51:45) Hiring the Right People (53:27) Identifying Red Flags in Interviews (54:51) The Importance of Self-Improvement (55:29) Curiosity and Adaptability in Candidates (56:36) Managing Through Crises: 9/11 and COVID-19 (01:02:12) Lessons from Early Career and Centerline Software (01:05:02) Founding Tripadvisor and Its Growth (01:18:03) Tripadvisor's Acquisition and Integration with IAC (01:25:23) Transitioning from Tripadvisor to Give Freely (01:27:26) The Vision and Impact of Give Freely (01:37:10) Conclusion and Final Thoughts   Show Notes: https://givefreely.com/ 
Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky   Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA   

EP 107: Steve Kaufer (Co-Founder, Tripadvisor) - Why He Left & What He’s Building Now

Since 2017, Bill Shufelt (CEO, Athletic Brewing) went from hedge fund trader to the CEO of the leading producer of non-alcoholic craft beer. Unlike the typical tech-focused chats, this one centers around a product many have fallen in love with. In the conversation, Bill tells stories of the unscalable but crucial strategies he used to build a brand, push past rejection, and redefine the non-alcoholic beer industry.   (00:00) Introduction to Athletic Brewing (00:52) The Early Days and Breakthrough Moments (01:15) Celebrity Partnerships and Brand Building (03:16) The Philosophy of Brand and Movement (07:33) The Non-Alcoholic Beer Market (10:46) The Entrepreneurial Journey and Personal Sacrifices (18:22) Scaling the Business and Marketing Strategies (28:20) Navigating Regulations and Health Trends (39:07) The Importance of a Tech Co-Founder (39:31) Home Brewing Beginnings (40:13) Innovative Brewing Process (41:13) Food Safety Challenges (43:24) Raising Funds and Building a Brewery (44:24) Vertical Integration Benefits (45:33) Early Sales Efforts (46:56) Investor Relations and Accountability (51:14) Long-Term Vision and Focus (01:00:10) Cultural Differences in Non-Alcoholic Beer (01:02:35) Health Considerations and Alcohol (01:10:38) The Sensation of Drinking (01:12:50) Reflections on the Entrepreneurial Journey (01:14:46) Conclusion and Final Thoughts
Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky   Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA   

EP 106: How Bill Shufelt Built Athletic Brewing - Every Plot Twist Along The Way

In the midst of meme stock craziness, Robinhood CEO Vlad Tenev shared his most eye-opening insights from running the company that transformed the game for retail investors. He talks about Robinhood’s new Gold Card, his views on crypto, the media side, how artificial intelligence could change finance, and more.   (00:00) Intro (03:27) The Origin of the Name 'Robinhood' (08:43) Navigating the GameStop and Meme Stock Saga (10:52) Rebuilding Trust and Brand Impact (19:10) Crisis Communication and Leadership Lessons (23:54) Industry Insights and Future of Trading (31:00) AI and Financial Services (33:34) Crypto and Regulatory Challenges (40:14) The Viral Launch of Robinhood (47:01) The Gold Card Launch and Customer Strategy (50:08) The Vision Behind Robinhood's Credit Card (53:50) Building vs. Buying: The X1 Acquisition (56:12) Integrating X1 into Robinhood (57:11) The GM Structure and Its Benefits (58:42) Challenges and Trade-offs of Decentralization (01:01:08) Financial Modeling and Customer Economics (01:04:48) Navigating Remote Work and Returning to the Office (01:09:14) Managing Stock Price Expectations (01:13:23) Hiring and Retaining Talent (01:17:11) Fundraising and Investor Relations (01:31:09) Launching Sherwood Media (01:38:56) Reflections and Future Aspirations
Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky   Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA   

EP 105: Vlad Tenev (CEO, Robinhood): The Meme Stock Crisis, The Future of Crypto, and AI Opportunities in Finance

On the day of the ChatGPT-4o announcement, Sam Altman sat down to share behind-the-scenes details of the launch and offer his predictions for the future of AI. Altman delves into OpenAI's vision, discusses the timeline for achieving AGI, and explores the societal impact of humanoid robots. He also expresses his excitement and concerns about AI personal assistants, highlights the biggest opportunities and risks in the AI landscape today, and much more.   (00:00) Intro (00:50) The Personal Impact of Leading OpenAI (01:44) Unveiling Multimodal AI: A Leap in Technology (02:47) The Surprising Use Cases and Benefits of Multimodal AI (03:23) Behind the Scenes: Making Multimodal AI Possible (08:36) Envisioning the Future of AI in Communication and Creativity (10:21) The Business of AI: Monetization, Open Source, and Future Directions (16:42) AI's Role in Shaping Future Jobs and Experiences (20:29) Debunking AGI: A Continuous Journey Towards Advanced AI (24:04) Exploring the Pace of Scientific and Technological Progress (24:18) The Importance of Interpretability in AI (25:11) Navigating AI Ethics and Regulation (27:26) The Safety Paradigm in AI and Beyond (28:55) Personal Reflections and the Impact of AI on Society (29:11) The Future of AI: Fast Takeoff Scenarios and Societal Changes (30:59) Navigating Personal and Professional Challenges (40:21) The Role of AI in Creative and Personal Identity (43:09) Educational System Adaptations for the AI Era (44:30) Contemplating the Future with Advanced AI
Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky   Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA   

EP 104: Sam Altman (CEO, OpenAI) talks GPT-4o and Predicts the Future of AI

After 18 years leading Guidewire (~$10B), Marcus Ryu made the transition from CEO to partner at Battery Ventures. In the episode, Marcus shares his journey of co-founding Guidewire in 2001, steering the company through its IPO in 2012, and building one of the largest vertical software businesses in the world. He shares his insights on how to build a durable company in troubling times, what he looks for in entrepreneurs, the future of vertical software, and much more.   (00:00) Intro (01:31) The Philosophical Approach to Investing and Strategy (03:27) Unpacking the Strategy: Diagnosis, Market Definition, and Execution (04:31) The Intricacies of Investment Decisions and Entrepreneurial Insight (10:39) From Philosophy to Silicon Valley: A Personal Journey (12:29) The Dot-com Bubble and Lessons Learned (26:19) Guidewire's Founding: Identifying a Niche in the Insurance Industry (37:13) The Early Days: Building from Scratch (37:34) The Founder's Balance Sheet: Energy, Time, and Market Demand (37:54) Starting with Nothing: The Humble Beginnings of a Startup (38:14) The Power of Insight and Precision in Startup Success (39:58) Product Development and Market Strategy: The Binder's Role (40:37) The Brutal Reality of Go-to-Market: Rejection and Resilience (42:59) The Parable of the Horse: Navigating Startup Highs and Lows (45:23) Overcoming Legal Battles and Finding a Moral Purpose (48:37) The CEO Transition: Learning from Leadership Changes (50:49) Foundational Principles for Sustaining Founder Relationships (53:41) Cultivating a Company Culture Based on Core Values (01:01:31) The Journey from Founder to Investor: A New Chapter (01:03:53) The Role of a Board and Achieving Founder-Investor Alignment (01:08:25) Managing Founder Psychosis and Scaling as a Leader (01:12:52) The Founder's Journey and Commitment (01:13:27) The Philosophical Underpinnings of Insurance (01:14:03) Insurance: A Civilizational Necessity (01:15:01) The Impact of Insurance on Society and Innovation (01:19:32) Navigating the Complexities of Insurance Regulation (01:21:07) The Dark Side of Ad Tech and Its Societal Impact (01:28:41) The Challenge of Communication and Leadership (01:31:46) The Future of Software: Vertical Specialization (01:42:05) Evaluating Founders and the Essence of Entrepreneurship (01:45:56) Emerging Opportunities and the Specificity of Markets (01:48:53) Concluding Reflections on Authentic Leadership
Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky   Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA   

EP 32: Former Twitter CEO Dick Costolo Talks About His Time at Second City, Running Twitter, and Missing Out on Instagram

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