Character AI's Annie Wickman on PMF, Google's Deal, and Humu

Annie Wickman shares insights from her journey as Google alum, first non-founder at Humu, and now Head of People at Character AI. Annie tackles our hardest questions in an unmissable episode. She covers the tensions between product-market fit and company culture, Character AI's unprecedented Google deal structure, taking the leap from people leader to a VC, and how to rebuild organizational trust.*Email us your questions or topics for Kelli & Nolan: [email protected] coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH ANNIE, NOLAN + KELLI ON LINKEDINAnnie: https://www.linkedin.com/in/annie-wickman-3332731/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINK/S:Character.AI: https://character.ai/—TIMESTAMPS:(00:00) Intro(01:17) Experience as First Non-Founder at Humu(03:16) Early Employee Challenges & Responsibilities(05:03) Why Annie Stayed at Humu for Four Years(06:30) Product Market Fit vs. Company Culture(09:05) When to Invest in Culture(11:15) Hiring the Right Leaders for Company Stage(11:40) Maintaining Morale When Company Isn't Winning(12:42) Transparency as Trust Builder(13:47) Sponsors: Planful | Metaview(16:47) Rebuilding Trust Through Honest Communication(19:11) Laszlo's Leadership Philosophy: Stretching People(21:02) Annie's Experience in Venture Capital at Forerunner(23:12) Teaching Founders to Fish vs. Providing Services(24:51) How to Evaluate VC Opportunities(26:09) Understanding VC Economics and Carry Structure(30:10) Character AI's Unprecedented Google Deal(32:56) Rebuilding Post-Acquisition: Product Vision Challenges(34:13) Annie's Perspective on the Deal Timeline(37:31) Post-Deal Reset: Napa Offsite and Hackathon(39:29) Employee Ownership After Acquisition(41:29) Building a New Culture While Keeping the Brand(42:11) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

In this week's 'Dear Heretics' segment, Kelli and Nolan discuss a listener's dilemma about working with ethically questionable founders. They explore the tension between startup rule-bending culture and personal values, advising that leadership requires either full alignment with founders or graceful departure.They reflect on the impossibility of compartmentalizing personal trauma, the importance of workplace support networks, and practical advice for both those experiencing crises and colleagues supporting them.*Email us your questions or topics for Kelli & Nolan: [email protected] coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—TIMESTAMPS:(00:13) Intro(00:52) Listener's Moral Dilemma with CEO (02:46) The Gamble With Me Philosophy (03:07) All In or All Out Leadership (04:09) Separating Morality from Alignment (04:38) The Danger of Staying When Misaligned (06:25) Toxic Without Knowing It (08:06) Modern Approach to Leadership Exits (08:53) Sponsors: Planful | Metaview (11:48) Is This Normal Startup Life? (12:07) Understanding Startup Rule-Bending (14:00) The Entrepreneurial Mindset (15:12) The Popsicle Stand Example (16:46) Building Your Leadership Brand (17:27) Working With vs Around Founders (18:19) The Lemonade Stand Rule (19:36) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

HR Heretics welcomes back guest Brett Queener, Managing Director at Bonfire Ventures, for a check in on the current venture landscape.Fresh from raising a $245 million fund, Queener explores how AI is fundamentally changing software companies, emphasizing the need for rapid iteration and questioning traditional playbooks. He shares thoughtful perspectives on evaluating AI startups beyond the hype, the changing nature of talent requirements, and why successful companies must embrace a "change economy" mentality to thrive.*Email us your questions or topics for Kelli & Nolan: [email protected] coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH BRETT, NOLAN + KELLI ON LINKEDINBrett: https://www.linkedin.com/in/brettqueener/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINKS:Bonfire Ventures: https://www.bonfirevc.com/—OTHER RECOMMENDED LINKS:The Change Economy: —TIMESTAMPS:(00:00) Intro (01:07) Bonfire's $245M New Fund (03:24) Today's Frothy AI Market (06:30) The 11X AI SDR Case Study (08:18) AI's Revolutionary Impact on Products (11:12) First-Time vs. Repeat Founders in AI (14:39) Sponsors: Planful | Metaview(17:38) Rethinking How Companies Operate (19:43) Hiring in the AI Era (22:58) Teams Getting Younger and AI Native (25:04) The Future of Junior Roles (28:22) The 11X Controversy Explained (30:29) Evaluating What's Real in AI Companies (33:29) Vibey Revenue and Real Value (37:00) Product Viability and Renewals (39:42) Assessing Founders and Products (42:10) The Case for In-Office Collaboration (44:31) The "Holy S**t" Product Moment (46:09) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

In this installment of AI Corner, Siadhal Magos, Metaview CEO, and Nolan Church dissect Anthropic's groundbreaking paper “Tracing the thoughts of a large language model” released on March 27, 2025. They explore surprising findings: LLMs plan ahead rather than simply predicting next tokens, think across multiple languages simultaneously, and often present explanations that satisfy humans rather than reflecting their actual reasoning processes.The conversation highlights the paradox of developing powerful AI systems without understanding their workings, raising implications for deployment, safety, and the "intelligence on tap" paradigm reshaping our technological relationship. We should all be paying attention.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH SIADHAL, NOLAN + KELLI ON LINKEDINSiadhal: https://www.linkedin.com/in/siadhal/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINKS:Anthropic’s featured paper: https://www.anthropic.com/news/tracing-thoughts-language-model Metaview: https://www.metaview.ai/—OTHER RECOMMENDED LINKS:Mercor: https://mercor.com/—TIMESTAMPS(00:13) Intro(00:45) Anthropic's Mind-Blowing Paper (01:37) LLMs Think Across Languages (02:04) Faked Reasoning in AI Models (02:28) AI Hallucinations Explained (03:00) First Paragraph Reveals Uncertainty (05:18) Beyond Next Token Prediction (07:23) Evaluating LLMs Without Understanding (08:44) More Human Than Software (10:05) Why You Should Experiment With AI (11:13) The Airplane Analogy (12:26) Safety Concerns for Future AI (12:54) Sponsors: Planful | Metaview(16:27) Dario Amodei on AI Self-Policing (18:05) OpenAI's $300B Valuation (19:33) Intelligence on Tap (22:02) Retraining Google Habits (24:35) Agentic AI & Reinforcement Learning (27:15) Human Training for AI Models (30:25) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

Today we're excited to introduce you to an episode of 10x Recruiting, a podcast from Metaview hosted by our very own Nolan Church. 10x Recruiting is focused on conversations with top talent leaders to help listeners build world-class teams and stay ahead in the evolving recruiting landscape.Today's guest is Arthur Matuszewski, who shares insights from his diverse career at Bridgewater, Better.com, and his firm Carrara. He emphasizes intellectual honesty, focusing on work outputs rather than titles, and avoiding false negatives in hiring. Nolan says he's one of the most insightful guests ever.Matuszewski advocates for evaluating talent based on actual value creation rather than pedigree, and stresses the importance of adapting recruitment strategies to each org's unique context rather than relying on standardized playbooks.Head to The 10x Recruiting Podcast on YouTube, Apple, or Spotify for more interviews like this one.YouTube: https://www.youtube.com/@10x_Recruiting_podApple: Spotify: —LINKS:Arthur’s LinkedIn: https://www.linkedin.com/in/arthurmatuszewski/Carrara: https://www.carrara.is/—TIMESTAMPS:(00:00) Intro(00:53) Episode preview (05:51) Arthur's career journey overview (07:53) Lessons learned at Bridgewater (10:41) Recruiting for teams vs individuals (12:35) Bridgewater's culture of experimentation (16:47) High attrition rate and false negatives (23:22) Better.com's rise and viral moment (28:02) Defining intellectual honesty (30:08) Carrara and focusing on the work (37:56) Balancing productivity with thinking time (40:03) Avoiding sunk costs in talent decisions (43:31) Carrara's process for delivering winners (45:43) Showing founders what the market is saying (47:19) Internal vs external talent perspectives (51:58) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

In this episode, Kelli Dragovich and Nolan Church are joined by Lucy Adams, founder of Disruptive HR. Adams critiques traditional HR's rigid policies, advocating instead for judgment-based approaches that treat employees as grown-ups. The conversation explores challenges facing HR business partners, the evolution of DEI initiatives, and how organizations can create environments where people thrive through high-trust cultures, rather than compliance-driven systems.*Email us your questions or topics for Kelli & Nolan: [email protected] coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Thatch makes it easy to give your team great healthcare. Save ~$1620 per employee yearly while giving them customizable plans. Visit https://thatch.AI/HR for a demo and receive a $100 gift card.Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH LUCY, NOLAN + KELLI ON LINKEDINLucy: https://www.linkedin.com/in/lucykadams/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINKS:Disruptive HR: https://disruptivehr.com/Lucy’s article “HR Business Partner: The toughest role in HR?”: https://disruptivehr.com/hr-business-partner-the-toughest-role-in-hr/—TIMESTAMPS:(00:00) Intro(01:17) Lucy's Background and BBC Experience(03:08) Personal Connection and BBC Stories(04:25) Origins of Disruptive HR(07:00) Evolution of HR and Post-COVID Workplace Changes(11:39) Trust and Autonomy in Workplace Decisions(16:56) Trust as Foundation for Business Success(17:32) Sponsors: Thatch | Planful(20:27) Progressive HR Policies and Examples(23:53) HR Business Partner Role Challenges(25:13) Sponsor: Metaview(27:55) Messy Reality of Great HR Work(31:00) HR's Focus on Process vs. Real Impact(33:26) Current HR Trends and Community Concerns(35:56) DEI Evolution and Conversation Approaches(45:53) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

In this week's 'Dear Heretics' segment, Kelli and Nolan discuss the profound impact of personal crises on work life. They share vulnerable stories about caring for ill family members—Kelli's mother's recent stage four cancer diagnosis and Nolan's father-in-law's illness and passing. They reflect on the impossibility of compartmentalizing personal trauma, the importance of workplace support networks, and practical advice for both those experiencing crises and colleagues supporting them.*Email us your questions or topics for Kelli & Nolan: [email protected] coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Thatch makes it easy to give your team great healthcare. Save ~$1620 per employee yearly while giving them customizable plans. Visit https://thatch.AI/HR for a demo and receive a $100 gift card. Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—TIMESTAMPS:(00:00) Intro (02:24) Impact of Crisis on Professional Life (03:19) Becoming a Parent to Your Parent (03:41) The Adrenaline Phase vs. Reality Setting In (04:18) Nolan's Story of His Father-in-Law (05:47) How Crisis Changes Your Perspective (07:11) The Impossibility of Compartmentalizing Life (08:02) The Importance of Strong Work Relationships (09:21) The Speed of Life-Changing Events (10:01) Gaining Wisdom Through Difficulty (10:18) The Value of Having a Coach (12:22) Using Your Support System Effectively (13:19) Finding a New Balance in Crisis (14:10) Practical Ways to Help Someone in Crisis (14:49) Sponsors: Thatch | Planful(17:00) Navigating the Healthcare System (18:03) The Critical Need for Medical Advocacy (19:35) How Crisis Impacts Your Work Priorities (20:17) Asking the Right Questions When Supporting Others (21:04) Sponsor: Metaview This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

In this week's 'Dear Heretics' segment, Nolan and Kelli discuss recent HR tech industry drama involving Rippling and Deel, where a "spy" from Deel allegedly infiltrated Rippling to steal competitive information.They describe Rippling's elaborate "honeypot" trap to catch Deel's corporate spy and how this incident exemplifies the evolution of business conflicts from private disputes to public social media spectacles, highlighting workplace transparency's growing complexity.*Email us your questions or topics for Kelli & Nolan: [email protected] coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsor:Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—TIMESTAMPS:(00:00) Intro(00:13) Deel and Rippling Drama(05:00) Rippling's Allegation: Spy in Dublin Office(06:19) The 'Honeypot' Trap Explanation(07:48) "That's Not a Honeypot, That's a Mousetrap"(09:00) Corporate Espionage More Common Than People Think(12:00) Going Public on Twitter as the "Master Stroke"(14:00) Sponsor: Metaview(16:16) New Era of CEOs Going to War(17:15) The Next Phase: Everything Is Public Now(19:24) The Spy Locks Himself in the Bathroom(22:04) Sunlight Is the Best Disinfectant This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

Nolan and Kelli welcome back friend of the pod David Hanrahan, who's just 60 days into his new role as CHRO at SolarWinds. The conversation kicks off with candid reflections on the Transform 2025 conference - the good, the bad, and what's missing from HR conferences today. They also dig into David's challenges and learnings transitioning to his new role, and a discussion on the changes coming for L&D initiatives.*Email us your questions or topics for Kelli & Nolan: [email protected] coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsor:Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH DAVID, NOLAN + KELLI ON LINKEDINDavid: https://www.linkedin.com/in/davidhanrahan/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINKS:Solarwinds: https://www.solarwinds.com/—TIMESTAMPS:(00:00) Introduction(00:37) David's Take on Transform(03:33) The Grittiness of HR(05:42) Value of In-Person Relationships(08:50) Transform's Community Session(10:36) Blackjack, Craps, and the Games(11:28) David's New Role at SolarWinds(15:35) Sponsor: Metaview(17:29) G Suite vs Microsoft Outlook(18:00) Juggling New Job Responsibilities(20:35) Katie Burke's Self Reflection(22:18) Painful Changes and Lessons from Multiple CHRO Roles(25:03) The Weird Moment for L & D(28:55) Effective Leadership Development(33:41) David's BHAG: Leadership Development(35:29) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

In another edition of 'Dear Heretics' Nolan and Kelli tackle talent calibration sessions. They address how HR needs to balance facilitation versus providing opinions and establish clear processes beforehand. They explore calibration's dual purpose: ensuring consistent evaluation standards and developing forward-looking talent plans. Above all, calibration needs to be an iterative process requiring transparency and company-wide understanding to avoid becoming toxic or misunderstood.*Email us your questions or topics for Kelli & Nolan: [email protected] coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsor:Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—TIMESTAMPS:(00:13) Intro(00:56) The Fine Line of HR Facilitation(01:46) Setting Process Rules Before Calibration(03:35) HR Should Opine with Objectivity(05:47) The New York Times Test(06:26) Sponsor: Metaview(08:20) Purpose of Calibration Sessions(09:37) Importance of Forward-Looking Discussions(10:35) Calibration Process Flow(12:16) Transparency Across the Company(13:10) Building the Calibration Muscle(14:27) Real-World Implementation(15:30) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com