Lenny RAG MCP Server

{ "episode": { "guest": "Ada Chen Rekhi", "expertise_tags": [ "Executive Coaching", "Founder Development", "Career Strategy", "Product Marketing", "Growth Marketing", "Subscriptions Business", "Women in Leadership", "Decision Framework", "Startup Operations" ], "summary": "Ada Chen Rekhi, executive coach and co-founder of Notejoy, discusses frameworks for making better career decisions through her signature \"Curiosity Loop\" methodology—a structured approach to gathering contextual advice from multiple people. She shares her own unconventional early career path spanning Microsoft, startup leadership, founding a contact management company acquired by LinkedIn, leading growth and subscriptions marketing at LinkedIn, and eventually becoming SVP of Marketing at SurveyMonkey. Ada emphasizes the importance of aligning career choices with personal values rather than external scorecards, applying explore-and-exploit strategies in early career development, and the nuanced realities of being a woman in Silicon Valley leadership. She also provides practical guidance on executive coaching, networking, and her experience co-founding multiple companies with her husband.", "key_frameworks": [ "Curiosity Loops - structured advice-gathering methodology", "Explore and Exploit - early career mode selection", "Inner Scorecard vs Outer Scorecard - decision-making lens", "Values Exercise - clarifying personal priorities", "Boiling Frog Metaphor - detecting workplace degradation", "Eating Your Vegetables - deliberate practice through discomfort", "Radical Candor - feedback delivery approach" ] }, "topics": [ { "id": "topic_1", "title": "Introduction to Ada Chen Rekhi and Curiosity Loops Framework", "summary": "Lenny introduces Ada and her background, then transitions to exploring her signature framework called Curiosity Loops - a structured methodology for gathering advice from multiple people to make contextual decisions. Ada explains the core concept: sending a specific, lightweight question to 5-10 carefully curated people and synthesizing their responses.", "timestamp_start": "00:00:00", "timestamp_end": "00:05:12", "line_start": 1, "line_end": 37 }, { "id": "topic_2", "title": "How to Structure Curiosity Loops Effectively", "summary": "Deep dive into the mechanics of Curiosity Loops, including crafting good questions (specific, unbiased, rationale-soliciting), selecting appropriate respondents (subject matter experts + people who know you), determining response rate expectations, and closing the loop with gratitude. Ada emphasizes the lightweight design principle and contrasts poor questions like \"what should I do with my career\" against better-formed ones with specificity and anchors.", "timestamp_start": "00:05:12", "timestamp_end": "00:15:43", "line_start": 37, "line_end": 105 }, { "id": "topic_3", "title": "Personal Values Exercise and Real-Time Application", "summary": "Ada guides Lenny through a values exercise where Lenny identifies his top personal values (adventure, optimism, kindness, growth, generosity, and discipline from his grandmother). They then apply these values in real-time to Lenny's current decision about what opportunities to pursue, discovering that his concept of \"adventure\" actually values doing less, simplifying, and prioritizing family time.", "timestamp_start": "00:16:51", "timestamp_end": "00:25:22", "line_start": 119, "line_end": 208 }, { "id": "topic_4", "title": "Early Career Strategy: Explore and Exploit Framework", "summary": "Ada shares her philosophy for optimizing early career development through the \"explore and exploit\" framework. She recounts her own journey: 367 days at Microsoft (exploration, learning corporate limitations), 3 years at Mochi Media startup (continued exploration, sampling marketing and product roles), founding Connected (exploration of entrepreneurship), being acquired by LinkedIn (transition to exploit mode focusing on specific learnings), and becoming SVP at SurveyMonkey at age 27-28 with a unique combination of experiences.", "timestamp_start": "00:25:55", "timestamp_end": "00:31:10", "line_start": 210, "line_end": 241 }, { "id": "topic_5", "title": "Recognizing When to Stay vs. Leave: The Boiling Frog Metaphor", "summary": "Ada addresses the tough question of knowing when to stick with an unfulfilling job and when to leave. She introduces the \"boiling frog\" metaphor - people often don't notice gradual deterioration of conditions until it's too late. The key lens is learning: are you growing and challenged daily, or hitting walls? If learning has stopped, proactively seek project changes, have conversations with leadership, or invest time in self-directed growth.", "timestamp_start": "00:32:01", "timestamp_end": "00:35:24", "line_start": 243, "line_end": 266 }, { "id": "topic_6", "title": "Balancing Resume Optimization vs. Personal Fulfillment and Values", "summary": "Lenny and Ada discuss the trap of endlessly optimizing one's resume and career trajectory - getting fancy logos, impressive titles, and credentials - while losing sight of actual fulfillment and values alignment. Ada shares her own journey of bailing out of the \"tiger parenting\" mindset of achievement optimization and using the values exercise to evaluate if her current trajectory served what actually mattered to her. She contrasts the \"inner scorecard\" (personal values) with the \"outer scorecard\" (external perception, status, wealth).", "timestamp_start": "00:36:31", "timestamp_end": "00:42:11", "line_start": 270, "line_end": 298 }, { "id": "topic_7", "title": "Executive Coaching: When It's Useful and When It's Not", "summary": "Ada takes a contrarian stance on coaching, arguing that most people don't actually need a coach and should explore alternatives first (mentorship, curiosity loops, online courses, community). However, coaching becomes valuable for founders in hyper-growth mode, sensitive interpersonal topics, and situations requiring accelerated learning. She emphasizes talking to 2-3 different coaches before committing, prioritizing personal connection over credentials, and potentially using multiple coaches for different specific goals (pitch coach, writing coach, parenting coach).", "timestamp_start": "00:42:42", "timestamp_end": "00:51:17", "line_start": 300, "line_end": 359 }, { "id": "topic_8", "title": "Being a Woman in Silicon Valley: Unwritten Rules and Physical Presentation", "summary": "Ada tackles the sensitive topic of being a woman in leadership in Silicon Valley by sharing a coaching story: a female seed-stage founder who didn't realize her casual appearance (old t-shirt, hair back, showing bra straps) was creating bias against her competence, especially going into fundraising. Ada gave her this hard feedback, the founder addressed it via a \"mini makeover,\" and received positive feedback about appearing more confident. Ada emphasizes that while the game is rigged, women can study the rules, help each other, and adapt rather than remaining powerless.", "timestamp_start": "00:52:03", "timestamp_end": "00:57:33", "line_start": 381, "line_end": 402 }, { "id": "topic_9", "title": "The Importance of Giving and Receiving Hard Feedback", "summary": "Building on the coaching story, Ada and Lenny discuss the difficulty of giving feedback on sensitive topics (appearance, physical presentation, immigrant experience) when there's no winning - managers avoid it to protect themselves and the employee. Ada references Sheryl Sandberg's experience with Radical Candor feedback about saying \"um,\" emphasizing that brave feedback-giving has real costs but immense value when framed with care about the person.", "timestamp_start": "00:57:37", "timestamp_end": "00:59:40", "line_start": 404, "line_end": 426 }, { "id": "topic_10", "title": "Eating Your Vegetables: Deliberate Practice Through Discomfort", "summary": "Ada introduces \"eating your vegetables\" - the concept that children need 10-12 exposures to vegetables before developing a taste for them. Applied to careers, this means distinguishing between disliking something because you're bad at it versus genuine dislike. Ada shares her own example: being awkward at networking in Silicon Valley, so she created a rule to attend weekly events, hand out 10 business cards introducing herself, and touch the back wall before leaving. After a few weeks, it became easier, and those early relationships became foundational.", "timestamp_start": "00:59:55", "timestamp_end": "01:03:24", "line_start": 430, "line_end": 449 }, { "id": "topic_11", "title": "Content Creation and Modern Networking as Vegetables", "summary": "Ada expands on eating-your-vegetables examples relevant to modern careers: LinkedIn 30-day posting challenges for overcoming the awkwardness of sharing content, and the deliberate practice of reaching out to interesting people via DMs. The key is moving from one failed attempt to a pattern of 10-12 tries to learn what works, rather than giving up after initial discomfort.", "timestamp_start": "01:04:34", "timestamp_end": "01:05:59", "line_start": 450, "line_end": 465 }, { "id": "topic_12", "title": "Authenticity in Content Creation and Writing", "summary": "Lenny and Ada discuss reframing content creation from seeking followers/likes to crystallizing genuine thoughts and sharing useful insights. Ada recommends \"writing for an audience of one\" - imagine a trusted colleague and write for them. This reduces obsession with outcomes and increases authenticity, which people detect and appreciate. The framing shifts from self-promotion to sharing something genuinely useful.", "timestamp_start": "01:05:59", "timestamp_end": "01:06:53", "line_start": 463, "line_end": 471 }, { "id": "topic_13", "title": "Co-Founding a Company with Your Partner: Pros, Cons, and Conditions", "summary": "Ada shares her experience co-founding Notejoy with her husband Sachin. Initially enthusiastic, she now acknowledges it's either \"really well or really badly\" with no middle ground. Success factors: (1) Complementary domains and clear decision-making rights (Sachin owns product/design/engineering, Ada owns marketing/operations/finance), (2) Ability to engage in constructive conflict by attacking problems not each other, (3) Taking feedback objectively rather than personally, (4) Prioritizing the relationship through explicit check-ins like 30-60-90 day relationship health discussions.", "timestamp_start": "01:07:10", "timestamp_end": "01:10:58", "line_start": 473, "line_end": 503 }, { "id": "topic_14", "title": "Lightning Round: Book Recommendations", "summary": "Ada recommends two books: (1) \"Persuasion\" by Robert Cialdini for understanding persuasion strategies useful in marketing, founding, and product design, (2) \"Designing Your Life\" by Bill Burnett and Dave Evans from Stanford Design School, which applies design thinking to life and career planning for creating paths that are both meaningful and successful.", "timestamp_start": "01:11:17", "timestamp_end": "01:12:23", "line_start": 517, "line_end": 528 }, { "id": "topic_15", "title": "Lightning Round: Entertainment and Media Preferences", "summary": "Ada discusses her favorite recent media: Ted Lasso (current season), and particularly Star Trek: Strange New Worlds, which she praises for balancing interesting adventures with resolution and happiness, not always defaulting to conflict and danger. She appreciates that some episodes end happily without catastrophe, adding a missing element to modern television storytelling.", "timestamp_start": "01:12:25", "timestamp_end": "01:13:28", "line_start": 530, "line_end": 552 }, { "id": "topic_16", "title": "Lightning Round: Interviewing Approach and Products", "summary": "Ada shares her favorite interview question: \"What's a common misconception people have about you?\" - useful for resetting bias and assessing self-awareness. For products, she highlights Notejoy (her company, used for roadmaps and coaching notes), Captio (iOS app for brain dumps), and Arc (new browser addressing browser tab problems). Lenny counters with Note to Self app as even simpler alternative.", "timestamp_start": "01:13:37", "timestamp_end": "01:15:11", "line_start": 554, "line_end": 568 }, { "id": "topic_17", "title": "Lightning Round: Productivity Tip - The Five-Minute Start", "summary": "Ada's core productivity advice: the night before, identify the one thing you need to accomplish. Then at the earliest opportunity, commit just five minutes to starting it. This overcomes productive procrastination - the tendency to do other important-but-not-essential tasks instead. She finds five minutes reliably turns into an hour of focused work because starting is the mental hurdle. Similar to \"The Highlight\" framework from Make Time book.", "timestamp_start": "01:15:43", "timestamp_end": "01:17:01", "line_start": 570, "line_end": 586 }, { "id": "topic_18", "title": "Closing: How to Find Ada and Her Work", "summary": "Ada provides contact information: Twitter/LinkedIn (@adachen), adachen.com, and adachen@gmail.com. She invites feedback, riffs on ideas discussed, and offers to discuss coaching with interested founders. Notejoy is available at notejoy.com. Lenny thanks her and concludes the episode.", "timestamp_start": "01:17:21", "timestamp_end": "01:18:01", "line_start": 588, "line_end": 605 } ], "insights": [ { "id": "I1", "text": "Curiosity loops fight bad advice by making advice contextual. Generic advice like 'quit your job and chase your dreams' or 'grind first and build experience' only works in certain contexts - curiosity loops help you determine which applies to your specific situation.", "context": "Explaining why curiosity loops are useful", "topic_id": "topic_2", "line_start": 38, "line_end": 43 }, { "id": "I2", "text": "A good question must be specific, solicit rationale, and avoid bias. 'What should I do with my career?' is too vague and puts cognitive load on respondents. Better: 'I'm a marketer thinking of doing a webdev bootcamp - is that a good idea?' because it provides anchors to explore.", "context": "Discussing question structure in curiosity loops", "topic_id": "topic_2", "line_start": 42, "line_end": 48 }, { "id": "I3", "text": "Helping someone feels good, and when you tell them later that their advice changed your life or your decision, it reinforces the positive feeling. This makes asking for input reciprocal and valuable for both parties, not just transactional.", "context": "Why closing curiosity loops with gratitude matters", "topic_id": "topic_2", "line_start": 52, "line_end": 54 }, { "id": "I4", "text": "When using curiosity loops, look for hard feedback, surprises, and things you strongly disagree with. These are signals that you may have missed something in your decision-making process - similar to user research, curiosity loops are about looking around the corner, not following orders.", "context": "How to interpret curiosity loop feedback", "topic_id": "topic_2", "line_start": 103, "line_end": 105 }, { "id": "I5", "text": "Executive function - the ability to make decisions and be thoughtful - peaks at age 30 and declines afterward. This is relevant when making major life decisions like estate planning, as it affects the age at which someone should gain full control of assets.", "context": "Using curiosity loops for personal decisions like estate planning", "topic_id": "topic_2", "line_start": 67, "line_end": 80 }, { "id": "I6", "text": "Your values are an internal scorecard that shows what truly matters to you, distinct from the external scorecard of status, money, and others' perception. Decisions should be evaluated against your values, not the external scorecard.", "context": "Purpose of the values exercise", "topic_id": "topic_3", "line_start": 122, "line_end": 123 }, { "id": "I7", "text": "When you decompose abstract values like 'adventure' into what they actually mean to you, you may discover that some seemingly obvious career opportunities don't align. Writing a book might seem adventurous initially but becomes a treadmill of endless creation - not actually aligned with the adventure value.", "context": "Applying values to real decisions", "topic_id": "topic_3", "line_start": 161, "line_end": 165 }, { "id": "I8", "text": "Career paths that look objectively better (bigger title, higher status, more impressive) can actually be worse for your happiness if they oppose your core values. It's possible to sacrifice values like relationships, autonomy, and growth in pursuit of external validation.", "context": "Ada's personal example of turning down high-profile opportunity", "topic_id": "topic_6", "line_start": 172, "line_end": 176 }, { "id": "I9", "text": "Early career success comes from exploring with a thesis - having hypotheses about what you enjoy and what works for you, then testing them through varied roles and industries rather than committing to one path too early.", "context": "Explore and exploit framework", "topic_id": "topic_4", "line_start": 218, "line_end": 223 }, { "id": "I10", "text": "In exploit mode (when you've found something rich), be intentional about which aspects you deepen rather than defaulting to title/team size/compensation. Ada chose to learn growth and subscriptions at LinkedIn instead of pursuing a big promotion, because those learnings served her future founding goals.", "context": "Exploit mode decision-making at LinkedIn", "topic_id": "topic_4", "line_start": 231, "line_end": 239 }, { "id": "I11", "text": "The boiling frog problem in careers: people rationalize staying in jobs that are slowly getting worse by telling themselves 'it'll get better' or 'I'm one promotion away.' You need to actively monitor whether you're learning and growing, not just assume inertia is patience.", "context": "Recognizing when to leave a job", "topic_id": "topic_5", "line_start": 243, "line_end": 251 }, { "id": "I12", "text": "If you're not learning in a role where you're otherwise performing well, proactively seek change: have conversations with leadership about new projects, find opportunities to stretch yourself, or use the extra time you have to build relationships or learn skills independently.", "context": "Active strategies within a job that isn't serving learning", "topic_id": "topic_5", "line_start": 250, "line_end": 255 }, { "id": "I13", "text": "Inner scorecard vs outer scorecard: your inner scorecard measures things like how you spent your day, how good of a person you are, whether you had adventure. Your outer scorecard measures status, wealth, top 10 lists. These often conflict, and you must consciously choose which to optimize for.", "context": "Warren Buffett framework for decision-making", "topic_id": "topic_6", "line_start": 289, "line_end": 296 }, { "id": "I14", "text": "Most people do not need a coach. Before hiring one, explore alternatives: mentorship, curiosity loops, online courses (like Reforge), communities. Coaching is best for founders in hyper-growth, sensitive interpersonal topics, and situations requiring accelerated learning and personal connection.", "context": "Ada's contrarian take on coaching", "topic_id": "topic_7", "line_start": 301, "line_end": 314 }, { "id": "I15", "text": "Talk to 2-3 different coaches before committing. Half of founders hire their friend's coach without exploration. Connection and vibe matter more than credentials. Different coaches have different styles (structured vs unstructured, teaching vs frameworks), and what works for others may not work for you.", "context": "How to select a coach", "topic_id": "topic_7", "line_start": 328, "line_end": 339 }, { "id": "I16", "text": "Like sports athletes with multiple coaches (offensive coach, defensive coach, swing coach), you can benefit from multiple executive coaches for different goals: a pitch coach for fundraising, a writing coach for specific projects, in addition to broader executive coaching.", "context": "Multi-coach approach for high performers", "topic_id": "topic_7", "line_start": 340, "line_end": 342 }, { "id": "I17", "text": "The rules of professional success in Silicon Valley are unwritten and unsafe to discuss (like physical appearance affecting credibility). While the game is rigged, women are not powerless - they can study the rules, help each other, and adapt rather than ignoring these biases.", "context": "Being a woman in leadership", "topic_id": "topic_8", "line_start": 393, "line_end": 402 }, { "id": "I18", "text": "Managers rarely give feedback on appearance or physical presentation to women because there's 'no winning' - they risk being perceived as biased or inappropriate. This leaves women unaware of how their presentation affects perception and credibility, especially in high-stakes situations like fundraising.", "context": "Why hard feedback on appearance is avoided", "topic_id": "topic_9", "line_start": 393, "line_end": 396 }, { "id": "I19", "text": "Good feedback is delivered with both care ('I respect you so much') and directness ('here's what's limiting you'). The feedback is more effective when it identifies controllable, easy-to-fix elements rather than immutable traits.", "context": "Radical Candor approach in coaching", "topic_id": "topic_9", "line_start": 410, "line_end": 426 }, { "id": "I20", "text": "Children need 10-12 exposures to something new before developing a taste for it. In careers, this means distinguishing between 'I dislike this because I'm bad at it' versus 'I genuinely dislike this.' You must persist through initial discomfort to accurately assess true fit.", "context": "Eating your vegetables concept", "topic_id": "topic_10", "line_start": 436, "line_end": 446 }, { "id": "I21", "text": "Productive procrastination is when you do other important tasks to avoid the one most important task. Five minutes is a sufficient commitment to overcome the mental hurdle of starting. Once started, five minutes often turns into sustained focus because the barrier was psychological, not actual difficulty.", "context": "Overcoming avoidance through small commitments", "topic_id": "topic_10", "line_start": 571, "line_end": 573 }, { "id": "I22", "text": "LinkedIn posts and online content feel cringey when the intent is self-promotion or audience-building. Reframing as 'I want to crystallize a thought I have and share something useful' removes the awkwardness and increases authenticity, which resonates more with readers.", "context": "Overcoming content creation resistance", "topic_id": "topic_12", "line_start": 461, "line_end": 465 }, { "id": "I23", "text": "Write for an audience of one - imagine you're talking to a trusted colleague. This avoids over-fixation on follower counts and outcomes, focusing instead on sharing genuinely interesting ideas. The most engaging content comes from reduced effort to appear impressive.", "context": "Content creation advice", "topic_id": "topic_12", "line_start": 464, "line_end": 467 }, { "id": "I24", "text": "Co-founding with a partner is extremely volatile - it either goes very well or very badly with no middle ground. Success requires: (1) complementary domains with clear decision-making rights, (2) ability to separate feedback on ideas from feedback on the person, and (3) prioritizing the relationship.", "context": "Co-founding dynamics", "topic_id": "topic_13", "line_start": 481, "line_end": 492 }, { "id": "I25", "text": "In partnerships, constructive conflict requires attacking the problem, not the person. When a partner says your work isn't good, interpret it as 'the plan needs improvement' not 'you're bad.' This truth-seeking mindset, focused on business outcomes, is crucial for working with partners or close collaborators.", "context": "Managing interpersonal dynamics in co-founding", "topic_id": "topic_13", "line_start": 487, "line_end": 492 } ], "examples": [ { "id": "E1", "explicit_text": "when I was working at SurveyMonkey in the past, I had this opportunity to spend a lot of time with the survey researchers, and we really talked a lot about what makes a question good", "inferred_identity": "SurveyMonkey - market research and survey tools company", "confidence": "explicit", "tags": [ "SurveyMonkey", "research", "surveys", "questionnaire design", "B2B SaaS", "customer feedback", "workplace learning" ], "lesson": "Learning rigorous question design from expert researchers (specificity, rationale, bias reduction) applies broadly to gathering advice and insights", "topic_id": "topic_2", "line_start": 41, "line_end": 43 }, { "id": "E2", "explicit_text": "At my first job, which was basically this entry level sales job at Microsoft, working on Microsoft adCenter", "inferred_identity": "Microsoft - technology company, adCenter product (advertising platform)", "confidence": "explicit", "tags": [ "Microsoft", "AdCenter", "advertising", "sales", "enterprise technology", "corporate environment", "entry-level role" ], "lesson": "Fast-paced startup environments appeal to those who find corporate life too slow-paced. 367 days at Microsoft taught Ada that corporate culture wasn't right for her entrepreneurial mindset.", "topic_id": "topic_4", "line_start": 212, "line_end": 219 }, { "id": "E3", "explicit_text": "I moved to this series a startup where I had to sample my desk on the first day called Mochi Media", "inferred_identity": "Mochi Media - gaming/advertising startup", "confidence": "explicit", "tags": [ "Mochi Media", "startup", "games", "marketing", "product", "three-year tenure", "dynamic team" ], "lesson": "Testing multiple roles (marketing and product) within a startup environment to discover strengths and preferences. Mochi Media validated Ada's love of marketing and small-team dynamics but prompted her to explore founding.", "topic_id": "topic_4", "line_start": 220, "line_end": 230 }, { "id": "E4", "explicit_text": "I founded Connected, and Connected was this personal CRM that's a little bit like Clay", "inferred_identity": "Connected - personal CRM startup (inferred: founded by Ada Chen Rekhi during her founder exploration phase)", "confidence": "explicit", "tags": [ "Connected", "CRM", "contact management", "personal network management", "startup founder", "B2C SaaS", "founder experience", "acquisition" ], "lesson": "Founding a company taught Ada entrepreneurship and provided learnings she'd bring to future ventures. Connected was acquired by LinkedIn, validating the founding hypothesis and enabling transition to exploitation mode.", "topic_id": "topic_4", "line_start": 221, "line_end": 231 }, { "id": "E5", "explicit_text": "After Connected was acquired by LinkedIn, I moved into this exploit mode. So I was at LinkedIn for a period of time while I was investing, and I really wanted to be intentional about the time that I spent there", "inferred_identity": "LinkedIn - professional social network company", "confidence": "explicit", "tags": [ "LinkedIn", "acquisition", "growth marketing", "subscriptions", "founder learning", "large enterprise", "strategic role selection" ], "lesson": "Rather than pursuing promotion and management, Ada strategically selected roles at LinkedIn (growth marketing, subscriptions) to fill knowledge gaps from her founder experience. This intentional exploit strategy made her a valuable hire for SurveyMonkey.", "topic_id": "topic_4", "line_start": 230, "line_end": 240 }, { "id": "E6", "explicit_text": "I really wanted to be intentional about the time that I spent there in terms of how I wanted to exploit it... my role at LinkedIn was really explicit. I even told my manager this when I first came in, 'I'm here to learn to be a better founder.'", "inferred_identity": "LinkedIn - Ada's internal mindset and career strategy at LinkedIn", "confidence": "explicit", "tags": [ "LinkedIn", "growth", "subscriptions", "intentional learning", "transparency with management", "founder preparation", "strategic role selection" ], "lesson": "Being transparent with management about specific learning goals (growth, subscriptions, pricing) rather than pursuing traditional advancement (title, team size) can lead to more valuable roles that serve your long-term plans.", "topic_id": "topic_4", "line_start": 233, "line_end": 239 }, { "id": "E7", "explicit_text": "the fact that I was a startup founder. I had big company experience. I had growth experience, and I had subs experience. And I was a product marketer. That was actually the winning combination that caused SurveyMonkey to send me a LinkedIn InMail, start a conversation and ultimately bring me in as their head of marketing", "inferred_identity": "SurveyMonkey - survey and customer feedback platform", "confidence": "explicit", "tags": [ "SurveyMonkey", "SVP of Marketing", "executive role", "age 27-28", "founder background", "growth expertise", "subscriptions expertise" ], "lesson": "Strategic accumulation of diverse experiences (startup founding, growth marketing, subscriptions, large company scale) makes you attractive to companies needing those specific skills. SurveyMonkey valued Ada's combination more than her lack of management experience.", "topic_id": "topic_4", "line_start": 239, "line_end": 241 }, { "id": "E8", "explicit_text": "It was this step where I could do something that was, at the time, really high profile and really exciting and felt great, but also involved demanding travel and grueling hours. And wasn't in a space that I was excited about, but it looked amazing on my resume.", "inferred_identity": "High-profile opportunity Ada turned down (context suggests executive role, not identified)", "confidence": "implicit", "tags": [ "high-profile role", "resume optimization", "travel demands", "grueling hours", "values misalignment", "outer scorecard pressure", "career inflection point" ], "lesson": "Seemingly perfect opportunities for external validation can actually undermine personal values. Using the values exercise revealed that this role would fail on her top three values despite being impressive on a resume.", "topic_id": "topic_6", "line_start": 283, "line_end": 285 }, { "id": "E9", "explicit_text": "I was working with a seed stage founder, and she's so smart... She's one of those people that is just stellar... We met together for the first time in person at lunch. I feel almost nervous talking about this here. The disparity between my sense of who she was as an operator and how she came across to me initially at this lunch was really striking in that it was a weekday lunch and she was dressed as if she was hanging out on the weekend. So old T-shirt, hair back and in a claw, bra straps were showing.", "inferred_identity": "Seed-stage founder (Ada's coaching client) - identity anonymized per coaching confidentiality", "confidence": "implicit", "tags": [ "seed stage founder", "female founder", "physical appearance", "bias and credibility", "fundraising", "coaching insight", "unwritten rules" ], "lesson": "Competent female founders often don't receive feedback on how their physical presentation affects initial credibility and perception in professional contexts. Hard feedback delivered with care can be transformative, especially pre-fundraising.", "topic_id": "topic_8", "line_start": 383, "line_end": 389 }, { "id": "E10", "explicit_text": "Her reaction was like, 'Oh my God, Ada. No one has ever connected the dots for me. Thank you so much. It has never explicitly been told to me that some of these elements which you describe, and they're very easy for me to fix and I'm motivated to fix them, are things that might actually trigger certain impressions or biases.'", "inferred_identity": "Same seed-stage founder from E9", "confidence": "implicit", "tags": [ "seed stage founder", "female founder", "feedback reception", "bias awareness", "fundraising impact", "empowerment through feedback", "controllable elements" ], "lesson": "When hard feedback identifies controllable, fixable elements (not immutable traits), founders appreciate and act on it. She later reported increased positive feedback about appearing 'more confident and more energetic' after the makeover.", "topic_id": "topic_8", "line_start": 390, "line_end": 393 }, { "id": "E11", "explicit_text": "I had to go out once a week for a couple of months, go to an external event, and I would count out 10 business cards. And the rule was, I had to hand out all 10 of those business cards by introducing myself to people that were new, and touch the back wall of the venue of that event and then I could leave.", "inferred_identity": "Ada's early networking practice (early in Silicon Valley career, likely 2000s)", "confidence": "explicit", "tags": [ "networking", "Silicon Valley", "early career", "deliberate practice", "discomfort exposure", "structured rule", "business cards" ], "lesson": "Deliberate, structured practice with constraints (10 business cards, touch back wall) forced Ada through initial networking awkwardness. Several of those early relationships became foundational to her network.", "topic_id": "topic_10", "line_start": 440, "line_end": 444 }, { "id": "E12", "explicit_text": "I know a lot of people have talked about doing a LinkedIn 30. So 30 days of posting something on LinkedIn in terms of content every day for 30 days straight, and just getting past that barrier of sharing.", "inferred_identity": "LinkedIn 30 challenge - emerging trend in content creation coaching", "confidence": "explicit", "tags": [ "LinkedIn", "content creation", "deliberate practice", "daily posting", "barrier to sharing", "personal branding", "habit building" ], "lesson": "The LinkedIn 30 challenge demonstrates eating-your-vegetables principle: people find daily posting awkward and self-promotional initially, but repetition reveals what resonates and builds authentic voice.", "topic_id": "topic_11", "line_start": 451, "line_end": 453 }, { "id": "E13", "explicit_text": "We've actually had a couple of friends try it, and it's been such a mixed bag of results... My personal experience is I love it. My partner Sachin, and I work really well together.", "inferred_identity": "Sachin (Ada's husband) - co-founder of Notejoy", "confidence": "implicit", "tags": [ "Notejoy", "co-founder marriage", "husband-wife founding", "complementary skills", "successful partnership", "mixed outcomes for others" ], "lesson": "Co-founding with a spouse is highly variable - either works very well (Ada and Sachin's case) or very badly. Success depends on complementary skills, clear domains, and ability to separate criticism of ideas from criticism of person.", "topic_id": "topic_13", "line_start": 482, "line_end": 490 }, { "id": "E14", "explicit_text": "So Sachin does product design and engineering. I focus on marketing, operations, finance, everything else on the business side.", "inferred_identity": "Sachin (Ada's husband/co-founder) and Ada's role division at Notejoy", "confidence": "explicit", "tags": [ "Notejoy", "role clarity", "complementary skills", "product design", "engineering", "marketing operations", "decision-making rights" ], "lesson": "Clear domain separation (Sachin owns product/design/engineering, Ada owns business/marketing/finance) prevents conflict over decisions and enables confident leadership in each area.", "topic_id": "topic_13", "line_start": 485, "line_end": 488 }, { "id": "E15", "explicit_text": "I even told my manager this when I first came in, 'I'm here to learn to be a better founder'... I'd built LinkedIn into grow marketing for LinkedIn, working with their growth team from a hundred million to 200 million members", "inferred_identity": "LinkedIn growth team - scaling from 100M to 200M members", "confidence": "explicit", "tags": [ "LinkedIn", "growth marketing", "growth team", "scale", "100M members", "200M members", "experiment design" ], "lesson": "Working on growth at LinkedIn during explosive scaling phase provided rare opportunity to learn at massive scale, from experiment design to financial optimization.", "topic_id": "topic_4", "line_start": 236, "line_end": 237 }, { "id": "E16", "explicit_text": "then shifted into the subscription side where I worked on LinkedIn subscriptions and ran their sales subscriptions business at scale through the online channel", "inferred_identity": "LinkedIn subscriptions business - building premium tier", "confidence": "explicit", "tags": [ "LinkedIn", "subscriptions", "business model", "premium features", "sales enablement", "SaaS monetization", "financial planning" ], "lesson": "Moving from growth to subscriptions at LinkedIn taught Ada SaaS monetization, pricing strategy, and how to balance acquisition with retention - knowledge she brought to SurveyMonkey.", "topic_id": "topic_4", "line_start": 236, "line_end": 237 }, { "id": "E17", "explicit_text": "Persuasion by Robert Cialdini. I think it's a great book, if you're a marketer. It's a great book, if you're a founder or product person.", "inferred_identity": "Robert Cialdini - Persuasion (psychology book on influence principles)", "confidence": "explicit", "tags": [ "Persuasion", "Robert Cialdini", "psychology", "influence principles", "marketing", "product design", "founder toolkit" ], "lesson": "Understanding psychological principles of persuasion (consistency, reciprocity, authority, etc.) helps marketers and founders design products and businesses that resonate with people.", "topic_id": "topic_14", "line_start": 520, "line_end": 522 }, { "id": "E18", "explicit_text": "Designing Your Life, and it's out of the Stanford Design School. And it's by, let me look, Bill Burnett and Dave Evans. They're two Stanford D School professors, and what they're doing is they're applying design principles to life design.", "inferred_identity": "Designing Your Life by Bill Burnett and Dave Evans from Stanford Design School", "confidence": "explicit", "tags": [ "Designing Your Life", "Bill Burnett", "Dave Evans", "Stanford Design School", "life design", "career planning", "design thinking" ], "lesson": "Applying design thinking to your own life and career - generating multiple options, prototyping decisions, and iterating - leads to paths that are both meaningful and successful.", "topic_id": "topic_14", "line_start": 527, "line_end": 528 }, { "id": "E19", "explicit_text": "Ted Lasso is back, so I'm watching that, the newest season. I am also a Star Trek nerd, so I'm watching Star Trek: Strange New Worlds.", "inferred_identity": "Star Trek: Strange New Worlds - current Star Trek series", "confidence": "explicit", "tags": [ "Star Trek", "Strange New Worlds", "television", "science fiction", "storytelling", "optimism", "exploration" ], "lesson": "Ada appreciates Star Trek because it balances exploration with resolution and happiness, offering an alternative to the constant-conflict storytelling that dominates modern television.", "topic_id": "topic_15", "line_start": 533, "line_end": 540 }, { "id": "E20", "explicit_text": "What's a common misconception people have about you? I usually like to throw that in toward the end of the interview, and the reason why I think it's really useful is it's a way for me to reset my bias.", "inferred_identity": "Ada's interviewing practice (executive coach/founder hiring)", "confidence": "explicit", "tags": [ "interviewing", "bias reset", "self-awareness", "perception gap", "founder hiring", "executive coaching" ], "lesson": "Asking about misconceptions allows candidates to correct your first impressions and reveals self-awareness. It's a powerful tool for getting past initial bias in hiring or coaching assessment.", "topic_id": "topic_16", "line_start": 556, "line_end": 558 }, { "id": "E21", "explicit_text": "Notejoy is a fast and focused notes app for individuals and teams. So that's the company that I work on. So I use it for everything from Noora product roadmaps to my coaching notes, to even prepping for something like this podcast.", "inferred_identity": "Notejoy - Ada's current company, co-founded with husband Sachin", "confidence": "explicit", "tags": [ "Notejoy", "notes app", "productivity", "team collaboration", "product roadmaps", "coaching", "knowledge management" ], "lesson": "Notejoy serves multiple use cases - from product planning to personal knowledge management - demonstrating how a simple core product can support diverse workflows.", "topic_id": "topic_16", "line_start": 562, "line_end": 564 }, { "id": "E22", "explicit_text": "Another one that I really use a lot is Captio. It's been around for a while, but it's a little iOS app. I don't know if it's on Android, but basically it's a blank notepad. You can dump your brain into it, and there's one button, and it emails it to you.", "inferred_identity": "Captio - iOS notes app with email-to-self functionality", "confidence": "explicit", "tags": [ "Captio", "iOS", "notes app", "brain dump", "productivity", "capture tool", "asynchronous processing" ], "lesson": "Simple tools for capturing thoughts (Captio) serve a specific need - allowing quick brain dumps that get processed later, reducing cognitive load and context switching.", "topic_id": "topic_16", "line_start": 563, "line_end": 564 }, { "id": "E23", "explicit_text": "And then something that I just downloaded this week is Arc, the new browser. I'm actually really excited about its vision. I'm not sure if I'm going to work it into my workflow yet or how it fits in, but it's really beautiful and it's really cool to see someone iterating on the cluster that is browser tabs.", "inferred_identity": "Arc - new browser by The Browser Company", "confidence": "explicit", "tags": [ "Arc browser", "The Browser Company", "browser tabs", "productivity", "UI/UX", "tool evaluation" ], "lesson": "Ada appreciates thoughtful product design and innovation, even in mature categories like browsers. Arc's approach to solving tab management represents meaningful iteration.", "topic_id": "topic_16", "line_start": 566, "line_end": 567 }, { "id": "E24", "explicit_text": "I found another app, actually, the similar thing that I found even more simple. It's called Note to Self, just sits on my doc. Anytime I want to email myself a thought, I open it up and this type of thing. Somehow, it ends up being even easier.", "inferred_identity": "Note to Self - macOS app for emailing yourself notes", "confidence": "explicit", "tags": [ "Note to Self", "macOS", "notes app", "brain capture", "email to self", "minimalism", "productivity" ], "lesson": "Lenny counters Ada's Captio recommendation with an even simpler tool (Note to Self), demonstrating that simplicity often wins in productivity tooling.", "topic_id": "topic_16", "line_start": 569, "line_end": 569 } ] }