Perfect for founders and leaders tired of boring presentations, this episode is full with actionable tweaks.

Timestamped Segments

1. 00:02:54 - 00:05:10
   "The Pastor’s Secret: Non-Tech Origins"
   Vince reveals his background as a full-time pastor—weekly sermons forged his speaking chops and frameworks.
2. 00:08:00 - 00:09:16
   "Stage Fright? Nope, You Just Suck at Prep"
   Vince argues 90% of "nerves" stem from poor talk-writing, not fear. Key fix: Structure talks for memorability.
3. 00:15:00 - 00:17:09
   "Talk Ingredients: Why Ideas Alone Bomb"
   Breaks down the content spectrum (ideas → stories → tactics) and the "2-min rule" for pacing engagement.
4. 00:39:00 - 00:42:58
   "Open Strong: The 3Ps Hook Framework"
   Vince’s Pain Point → Problem → Promise method hooks audiences fast. Leah adds mnemonics for sticky concepts.

Hot Takes

1. “Stage Fright is a Cop-Out—Your Prep is the Real Problem”
   Vince insists most “nerves” vanish when talks are well-structured, pretested, and packed with analogies (not just ideas).
2. “Polished Performance is Overrated—Be a Lawyer, Not an Actor”
   Ditching theatrics for persuasion (e.g., “argue like you’re in court”) beats forced energy shifts for early-stage speakers.

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Timestamped Segments

1. 00:01:04 - 00:02:06
   "From Burnout to World Records"
   Anna’s background as a freediving athlete, multiple sclerosis survivor, and mentor to athletes and executives.
2. 00:02:54 - 00:05:10
   "Diagnosis & Denial: Early MS Struggles"
   Anna recounts her initial diagnosis at 20, early denial, and how MS symptoms worsened before she adopted lifestyle changes.
3. 00:08:00 - 00:09:16
   "The Turning Point: 2013 Crisis & Recovery"
   Anna Describes her health crisis, the realization of needing drastic changes, and how freediving became a tool for mental clarity.
4. 00:15:00 - 00:17:09
   "Practical Tools: Breathing, Boundaries, and Structure"
   Shares actionable strategies: 8-8-8 breathwork, daily habit structuring, and balancing work/rest priorities.
5. 00:39:00 - 00:42:58
   "Mental Mastery: Freediving Lessons for Leadership"
   Explains how freediving’s mental discipline (e.g., managing panic, trusting training) applies to high-pressure work environments.

Hot Takes

1. "Hustle Culture is a Lie – Your Body Knows Better"
   Anna critiques the "16-hour workday" myth, arguing that burnout stems from ignoring physical/mental limits. True productivity requires self-awareness and rest.
2. "Accountability ≠ Shame – It’s About Self-Compassion"
   Challenging the stigma around seeking help. Success isn’t about perfection but consistent, kind adjustments to habits and mindset.

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Timestamps

1. 00:01:38 - 00:07:00
   The elevator pitch crisis: Why outcomes aren’t enough.
2. 00:07:00 - 00:14:00
   Positioning anchors: Primary vs. secondary frameworks.
3. 00:14:00 - 00:25:00
   Differentiation: Linking problems to anchors.
4. 00:25:00 - 00:41:17
   Positioning pitfalls and real-world applications.

Hot Takes

🔥 "Product demos are the highest-value part of sales—not outcomes."
Anthony cites a study showing that for companies over $50M revenue, the product demo outweighed outcome-focused pitches.

🔥 "Most elevator pitches fail because they’re stacked secondary anchors."
Leading with outcomes like "we save time" without explaining what you actually do leaves listeners confused.

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Timestamps & Segments

• 00:00:00-00:07:00 | Data vs. Gut: The Product Leader’s Tightrope
  Larry’s framework for blending analytics with instinct in high-stakes decisions.
• 00:07:55-00:16:00 | Hiring Hack: Why 5-Minute Gut Checks Beat 9 Interviews
  How to spot A-players faster using presentation-based interviews and thin-slicing.
• 00:22:00-00:30:00 | Prototypes ≠ MVPs: Build to Spark Emotion, Not Just Data
  Why showing two excited customers beats a perfect metrics dashboard.
• 00:35:00-00:44:00 | Innovation Fuel: How to Sell Leadership (Not Features)
  Positioning products as category-defining tools instead of incremental updates.
• 00:44:00-00:54:00 | Budgeting Rebellion: Why Simplicity Trumps Spreadsheets
  Larry’s contrarian approach to financial planning that pissed off tinkerers (but worked).

Hot Takes
🔥 “If your prototype doesn’t make someone’s eyes light up in 5 minutes, kill it.”
🔥 “Hiring processes with more than three interviews are just cowardice in spreadsheet form.”

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Timestamps & Segments

1. 00:02:00 – From Lawyer to AI Disruptor
   Etie’s journey from predicting the 2008 crash to building AI that tackles agent burnout.
2. 00:09:00 – AI’s Hidden Superpower
   Why and how analyzing every customer conversation (not just samples) transforms decision-making.
3. 00:20:00 – Data Sanity vs. Stale Insights
   How Loris.AI keeps models dynamically updated—no more “cup of water in the ocean” bias.
4. 00:31:00 – The Chatbot Commoditization Trap
   Frontend bots are racing to the bottom; the real gold is in routing intelligence.
5. 00:38:00 – Enterprise AI’s Dirty Secret
   Why 2025 will force consolidation—and how CX leaders are becoming the new data powerbrokers.

Hot Takes
🔥 “AI agents using the same LLMs will have identical outputs within 2 years—it’s a race to the bottom.”
🔥 “If your AI isn’t making CX leaders the loudest voice in the boardroom, you’re doing it wrong.”

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It’s not about running more tests, but smarter ones.

Timestamps & Segments

00:01:02 – 00:10:00
The Experimentation Conundrum
Andres breaks down why most experiments fail, the "VC mindset" for testing, and why a 65% loss rate is better than industry standards.

00:10:05 – 00:20:00
Low Traffic, Big Swings
Strategies for companies with limited traffic: why timid tweaks waste time and how to bundle changes for measurable impact.

00:20:05 – 00:30:00
Redesigns: When to Rip the Band-Aid
Why most redesigns backfire, how to test without tanking metrics, and the political minefield of shipping "VP-approved" flops.

00:30:05 – 00:40:00
Storing (and Ignoring) Experiment Data
The lifecycle of experiment insights, why social proof is overrated, and how to avoid repeating past mistakes (hint: spreadsheets).

00:40:05 – 00:49:00
Hot Takes & Must-Reads
Andres’ controversial read on stale A/B testing dogma + book recs to overhaul your product playbook.

Hot Takes
🔥 “89% failure rate? You’re doing it right.” – Andres
🔥 “If stats aren’t significant after 4 months, ship it anyway—your samples are probably garbage.” – Leah

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🕒 Timestamps

00:02:28 - The Burnout Recipe
High-driven PMs + chaotic orgs = guaranteed burnout. It’s not your fault – it’s the cult of "ASAP" as a personality trait.

00:11:38 - Boundaries Aren’t B.S.
Why "I’ll just answer this Slack at 10 PM" destroys teams – and how to weaponize app blockers, second phones, and "No." as a full sentence.

00:18:46 - Leah’s ADHD Warfare
"Losing parking tickets is my superpower." Tactical tips for neurospicy PMs: rigid routines, external accountability partners.

00:27:28 - Leaders: Stop the Overwork Olympics
Why celebrating "Peter works 80-hour weeks!" backfires – and how to spot promotion-induced burnout traps.

00:40:41 - The Feedback Lie
"Improve your quant skills" vs. "Be more reliable" – why managers secretly crave PMs who say "This launch can wait".

00:46:26 - Burnout Doesn’t Care About Your Gender
Surprise! Men suffer equally – they just hide it better. The real divider? Whether your boss thinks "hustle" is a compliment.

00:52:14 - Exit Strategies
When to fix the org vs. flee – and how job hunting (even casually) boosts your boundary-setting muscles.

🔥 Hot Takes

1. "Burnout is a product problem – treat it like churn."
   If 72% of users quit, you’d fix the UX. Why blame PMs when 92% are drowning?
2. "Your 'high performer' is a liability."
   Promoting hustle addicts to leadership? Congrats – you just weaponized burnout.

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Timestamps & Key Moments

05:59 – AI: Innovation vs. Lipstick on a Pig
Why QuickBooks is losing to startups like Digits. Melissa’s rule: If AI doesn’t make the problem 10x easier, you’re just checking a box.

12:36 – Corporate Innovation’s Dirty Secret
Legacy companies fear self-disruption. Spin out autonomous teams with clear goals-not just “innovation theater” with beanbags and zero accountability.

20:19 – Boardroom Pressure & AI Hype
When investors demand AI, ask: Is this solving a real problem or chasing valuation multiples? Most boards care more about exit multiples than customer value.

24:33 – The “Latent Need” Blind Spot
Customers tolerate broken workflows (looking at you, QuickBooks). Spot problems people don’t even know they have.

29:55 – AI’s Mundane Superpower
Forget flashy chatbots-AI shines in automating daily struggles (e.g., Superhuman’s email shortcuts). If your team isn’t 10x faster, you’re doing it wrong.

44:10 – AI Ethics: When Algorithms Attack
Healthcare horror stories and why AI’s “brilliant insights” can backfire. Treat AI outputs as signals-not gospel-or risk ruining lives (and products).

Hot Takes

1. “AI Is a Terrible Strategist”
   Slapping AI on your product without solving a core customer problem is like putting a rocket engine on a horse cart. It’ll move faster… straight into a dumpster fire.
2. “Legacy Companies Are Their Own Worst Enemies”
   Corporate innovation fails because leaders prioritize protecting outdated revenue streams over killing them.
   If your “innovation team” isn’t scared of disrupting you, they’re not trying.

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Timestamps & Key Moments
00:00 - Intro to the Chaos
John’s AI-generated roast sets the tone: “Product management’s most unhinged mind” dissects why companies are glorified dumpster fires.

01:56 - Why Work Sucks
The “garbage can theory” of organizations: Companies aren’t rational machines—they’re battlegrounds for competing agendas. 30-50% of your team? Pragmatists who’ve stopped rocking the boat.

16:48 - Empowered Teams ≠ Chaos
Why autonomy beats bureaucracy: Faster decisions, local context, and fewer dependency hellscapes. Plus, the “mandate levels” model to avoid micromanagement meltdowns.

23:06 - Simplicity vs. Complexity
Leah’s restaurant metaphor: A simple menu (3 priorities max) beats a crowded one. Cutler counters: Complexity isn’t the enemy—bad interfaces are.

31:35 - The Physics of Scaling
Why SaaS companies implode: Multi-product sprawl and “sublinear complexity” myths. Spoiler: Design decisions > org charts.

40:49 - Force-Ranking Priorities
The dark art of saying “not this year” to shiny objects. Why your #4 priority is the silent killer.

49:32 - Skills for the Future
Read sociology, not another agile book. Cutler’s pick: Images of Organization to see companies as brains, prisons, or flux.

Hot Takes
🔥 “Your ‘A Players’ Are Mythical”
50% of your team is smart-but-checked-out pragmatists. Healthy? Maybe. Terrifying for founders? Absolutely.

🔥 Companies Are Organized Anarchies
Profit? Nah. Work is just humans negotiating needs. If your org chart looks rational, you’re lying to yourself.

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Timestamps

1. 00:00 – Intro: John’s journey from Google Ads to VC (and why tall founders have an edge)
2. 05:48 – “Vision-driven” is a red flag: Why early-stage startups should ditch grand visions for hypothesis-driven experiments.
3. 11:10 – The Foundation Sprint: Building a business case in 2 days (customer, problem, competitors, differentiation)
4. 23:34 – Slaying competitors (even if they’re “good enough”): Why substitutes and workarounds are your real rivals
5. 30:05 – Fake it ’til you validate it: Prototyping fake products to get real feedback (no coding required)1.
6. 39:48 – Case studies: How Slack, Gmail, and AI material science startups de-risk bets early1.
7. 45:50 – Closing: Why your MVP’s “surface area” matters more than polish (and where to find John’s book)

🔥 Hot Takes

1. “Vision-driven leaders are early-stage liabilities.”
   Hyping a “beautiful future” without validating assumptions? That’s a 50% failure rate waiting to happen
2. “Your pitch deck is probably BS.”
   Founders: If your “hypothesis” section is just buzzwords, you’re already behind. Investors want actionable experiments, not fairy tales

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Timestamps

02:23 – From SMB to Enterprise: Scaling Without Losing Vision
Rocketlane’s year-long stealth build focused on unifying project management, docs, and customer portals. The secret? Start with SMBs to validate core workflows before adding enterprise bells and whistles.

07:58 – Pricing for Outcomes, Not Seats
Why Rocketlane charges a premium over Asana: their customer portal drives faster time-to-value. But with AI automating workflows, Sri hints at consumption-based pricing coming soon.

22:32 – AI’s Role: Doing the Work, Not Just Organizing It
Charge for work done, not headcount, as teams shrink.

31:52 – The Compliance Trap
“Get SOC 2 early, even for SMBs.” Sri shares why skipping compliance torpedoes enterprise deals later. Pain now, payoff later.

37:37 – Roadmaps in the AI Era
Their moat? Owning the system of record for onboarding to build AI agents that competitors can’t replicate.

42:31 – Enterprise Demands vs. Vision
When some clients demanded features, Rocketlane delivered… 18 months later. Sri’s playbook: bake enterprise asks into broader platform goals to avoid becoming a custom dev shop.

🔥 Hot Takes

1. “MVPs are dead for established markets.”
   Sri’s radical bet: Launch full-featured products from day one in mature categories. Partial solutions get pigeonholed as “just another X”.
2. “SOC 2 isn’t optional—even for startups.”
   Compliance isn’t just for enterprises. Rocketlane prioritized SOC 2 early to avoid losing deals to legacy players. Painful upfront, critical long-term.

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Chapters with Timestamps

00:00–04:30

• The Vibes Economy: Why founders sell visions to investors but fail to communicate existential realities to their teams.
• The dangers of "pitch deck culture" infiltrating internal strategy.
• Matt's take: "Reality comes back to get you eventually."

04:30–15:00

• Product Teams vs. Corporate Reality: Why product managers need to embrace their role as business contributors.
• Leah and Matt discuss the importance of standing up to "Gary" (or sales) while staying revenue-focused.
• Gut vs. Data: Are vibes just pattern recognition in disguise?

15:00–28:00

• Simplifying Strategy: How Matt helps teams draw a direct line from their work to company goals.
• Christina Wodtke's "Radical Focus" approach: Orbiting company goals instead of cascading confusion.
• Real-world example: Turning multi-product chaos into measurable customer lifetime value gains.

28:00–40:00

• The Cost of Low Impact Work: Why Product Managers Must Think Beyond Their Immediate Team Resources.
• Leah’s rule of thumb: A team’s roadmap should aim for $3–5M in value annually.
• Survival Metrics vs. Success Metrics: Knowing when to kill a project before it drains resources.

40:00–52:00

• The Eye of Sauron Effect: Why teams avoid high-impact work and how to overcome it.
• Aligning incentives across teams and leadership to prioritize meaningful outcomes.
• Matt’s advice: Treat your CEO like a customer—help them tell the story that aligns work with business success.

52:00–End

• Long-Term Planning vs. Cadence Chaos: Balancing five-year plans with three-month cycles and monthly check-ins.
• Leah’s warning: Don’t let sales hijack long-term plans for enterprise promises.
• Final thoughts on commercially-minded PMs being the happiest (and most impactful) ones.

Key Quotes

1. Matt LeMay: "If you were the CEO, would you fund this team? Twice in my career, asking that question has prompted a team to proactively disband itself."
2. Matt LeMay: "Don’t wait for a perfect strategy from leadership; connect your work directly to what the business cares about most."

Resources Mentioned

1. Books:
   • Impact First Product Teams by Matt LeMay (available now).
   • Radical Focus by Christina Wodtke (for goal alignment strategies).
2. Key Concepts:
   • Survival Metrics (via Adam Thomas).
   • The "Eye of Sauron" phenomenon in corporate environments.

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Chapters with Timestamps

00:00-05:30 Meet the "Therapist for Type A Product Leaders" and the "Ops Whisperer"

• Tara Goldman's journey from VP of Product to coaching PMs on speaking executive
• Mackenzie Hughes' transition from GTM strategy to the "dark side" of product ops

05:30-15:00 The Great Disconnect: Why Product Teams Struggle with Business Impact

• The dangers of incentivizing output over outcomes
• Why most PMs can't answer "How much revenue do your ideas need to generate?"
• The critical importance of understanding churn at a granular level

15:00-30:00 Beyond Metrics: Building a Culture of Commercial Product Leadership

• Why having 40 metrics is worse than having none at all
• The power of driving a single metric through your entire organization
• Rethinking validation: "We've lost the art of experimentation"

30:00-45:00 The $5 Million Roadmap: Thinking Bigger (and Smarter) About Product Bets

• Why your product ideas need to generate 3-5x their cost (an article I recently wrote on this.)
• The counterintuitive truth: Bigger bets often require less upfront validation
• How to structure gates and learning milestones for major initiatives

45:00-60:00 Empowering Teams in an Age of Anxiety

• Why "empowered teams" is an overused term few actually implement
• How AI will shift the focus from shipping to go-to-market excellence
• Resources for product leaders looking to boost their business acumen

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Chapters with Timestamps

00:00–04:30

• From MLB dreams to Oracle’s cold call trenches: “My first prospect told me to blow him – and my manager said ‘that’s normal’”
• Why 2013 Vine videos mocking sales culture became accidental career fuel

04:30–15:00

• Influencer Economics 101: Turning “drowning in SaaS spam” into $500B brand partnership opportunities
• Why Salesforce pays him to clown CRMs: “They know I’ve suffered through 9,462 pipeline updates”

15:00–28:00

• AI’s Content Apocalypse: Why B2B marketers are “flooding the zone with bot-written bullshit”
• Survival Playbook: How to outlast AI-generated influencers and OnlyFans-for-CFOs nightmares

28:00–40:00

• The Algorithm Trap: Why LinkedIn rage bait dies faster than a SDR’s first quota
• Ross’s non-negotiables: “Never let brands own your content – unless they pay stupid money”

40:00–01:00:00

• Hot Takes: Why “product marketing language is corporate ASMR” and how to monetize exec foot pics (allegedly)

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Chapters with Timestamps

00:00–03:30

• Adam’s role at Mozilla: Building beyond Firefox, managing innovation, and why “killing projects” is critical.

03:30–15:30

• Stage Gating 101: How Mozilla’s framework prioritizes ideas, allocates resources, and avoids “innovation theater.”
• The 5 stages: Discovery, Exploration, Viability, Growth, and Sustaining.

15:30–30:00

• AI’s Double-Edged Sword: Turbocharging prototyping vs. drowning in “wrapper” tools.
• Why distribution (not product) is the new battleground for SaaS.

30:00–45:00

• Corporate Innovation Realities: Avoiding “software sprawl,” managing founder-minded PMs, and surviving existential pivots.
• Adam’s take on AI-driven sales tools: “We’re flooding the zone with crap.”

45:00–01:00:00

• Hot Takes: Why B2B SaaS companies built on “forms + databases” are doomed, and the future of AI agents.

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Key Timestamps

• 01:58 - Lidia’s unconventional path: From "business architect" to CPO roles at Spotify/Google
• 04:07 - Case Study: How "information architects" evolved into modern UX strategists
• 08:51 - Reality Check: "GPT-5 won’t fix human-centered leadership" (critical systems thinking)
• 14:21 - Data Point: 27 COBOL developer jobs in Sweden today (adaptation > prediction)
• 20:21 - Framework: Transferable skills that outlast tools (with PM/UX examples)
• 27:46 - Leadership Hack: Building "future-proof" teams through skill adjacency mapping
• 34:39 - Candid Talk: Why existential crises plague tech leaders (and how to reframe them)
• 42:02 - Tactical Takeaway: "Block 30 min/week for AI upskilling – no agenda required"
• 50:26 - Counterintuitive: "Stop future-proofing careers – start curiosity-proofing"

3 Strategic Themes for GTM Leaders

1. Navigating AI Disruption
   • Why AI adoption curves mirror mobile/web revolutions1
   • The critical human skills that remain automation-resistant (e.g., negotiation, prioritization)
2. Building Resilient Teams
   • Identifying "evergreen" skills (e.g., information architecture → modern UX strategy)1
   • Creating psychological safety for continuous reskilling
3. Personal Adaptation Playbook
   • Curated peer learning networks > generic upskilling platforms
   • Career capital vs. career comfort tradeoffs

Quotes

"Your ability to negotiate priorities with engineers/designers/execs is the ultimate transferable skill" – Lidia

"We don’t need future-proof careers – we need curiosity-proof humans" – Leah

Guest Background

• Current Role: CPO @ Gillian (building the world’s largest growth platform for founders)
• Career Highlights:
  • Scaled products at Spotify, Google, and Eschew
  • PhD in Human-Computer Interaction (early web/UX focus)
  • Pioneer in animated GIFs and 1990s web design

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Key Takeaways

1. AI Won’t Replace PMs, But It Will Change the Job: AI is a tool, not a threat. PMs who learn to use it effectively will thrive.
2. Start Small & Iterate: Don’t wait for the “perfect” AI solution. Experiment with tools like ChatGPT, Claude, and Whisper to find what works for you.
3. Cross-Functional Alignment Gets Easier: AI can surface insights from unstructured data, helping PMs align teams and avoid conflicts.
4. AI as a Thought Partner: Use AI to generate ideas, simulate scenarios, and streamline workflows—but always stay connected to the raw data.
5. The Future is Contextual: Tools like Notion AI and Slack AI are powerful because they have access to your company’s unique context.

01:36 - 04:16
Why Product Management Feels Less Fun (And AI Isn’t Helping)
Tal dives into why product management has become less enjoyable in recent years, citing increased pressure, fewer PMs per team, and the added uncertainty of AI. He emphasizes the importance of staying hands-on and experimenting with AI tools to cut through the noise.

04:16 - 07:59
AI’s Impact on PM Workflows: From Discovery to Go-To-Market
AI isn’t just changing how PMs work—it’s reshaping entire workflows, team structures, and even job applications. Tal breaks down the four key areas where AI is shaking things up and why PMs need to adapt quickly.

07:59 - 10:07
The Antidote to AI Fear: Small Experiments & Tinkering
Instead of fearing AI, Tal advocates for small, hands-on experiments. He shares practical tips for PMs to start tinkering with AI tools, like dedicating time each week to test new tools and iterate on prompts.

10:07 - 14:20
AI for User Research: Summarizing Transcripts & Building Craft
Leah and Tal discuss how AI can streamline user research, from summarizing transcripts to identifying key insights. Tal emphasizes the importance of iterating on prompts and staying connected to the raw data to maintain product intuition.

14:20 - 18:25
Trusting AI Outputs: When to Double-Check & When to Let Go
Leah shares a practical tip: test AI with data you already know well to gauge its accuracy. Tal adds that even when AI gets it right, PMs should still engage with the raw data to keep their intuition sharp.

18:25 - 22:54
Cross-Functional Alignment Made Easier with AI
AI can help PMs connect the dots across departments, like spotting conflicts between marketing campaigns and product launches. Tal and Leah discuss how AI can surface insights from unstructured data, making cross-functional collaboration smoother.

22:54 - 27:14
Building Custom AI Assistants: From SQL Queries to API Docs
Leah shares how she built a custom ChatGPT bot to handle SQL queries and API documentation, saving hours of manual work. Tal highlights the importance of giving AI context to make it truly useful.

27:14 - 29:53
AI Isn’t Magic: Start Small & Iterate
Tal debunks the myth that AI requires “magic spells” (aka perfect prompts) to work. He encourages PMs to start small, iterate, and not overthink the process.

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• "We need to reward effort, not just success."

01:20 - 07:30
Why Feedback Loops Fail (And How to Fix Them)
Julia breaks down why homogeneous feedback reinforces biases, the danger of “echo chambers,” and why SaaS teams need diverse perspectives to challenge assumptions.

07:30 - 14:45
Embodied Learning: The Science Behind VR, Physicality, and Retention
Deep dive into Julia’s research: How physical interaction (e.g., movement, touch) reshapes learning, why traditional education often misses the mark, and implications for SaaS product design.

14:45 - 22:00
From Theory to Practice: Actionable Strategies for Leaders
Tactical advice: Building resilient teams, designing experiments that embrace failure, and fostering curiosity over “convincing.” Includes Leah’s relatable analogies (e.g., gym consistency vs. learning).

22:00 - 28:50
The Emotional Side of Learning: Fear, Identity, and Incentives
Julia explains why emotional engagement matters (e.g., imposter syndrome, fear of failure), and how leaders can align incentives with sustainable learning processes.

28:50 - 33:00
Key Takeaways & Closing
Julia’s final wisdom: Why “explaining to understand” beats “explaining to convince,” and how SaaS leaders can start small (e.g., toy projects, cross-functional feedback).

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What does the future of marketing look like while everything changes so rapidly?

takeaways

• Influencer marketing is becoming less effective.

Sound Bites

• "The death of channels might be more accurate."
• "You have to figure out your strengths first."
• "You need to shut up about the other things."
• "Don't run your startup like an enterprise."

Chapters

00:00 Understanding Marketing Channels

05:06 The Evolution of Marketing

10:07 Influencer Marketing in B2B

15:13 Navigating the Noise of Social Media

19:58 Identifying Unique Marketing Advantages

25:13 The Importance of Focus in Marketing

26:39 Navigating Brand Messaging and Differentiation

29:02 The Importance of Focus in Marketing Strategies

31:11 Balancing Ideas and Execution in Marketing Plans

33:05 Marketing as a Product: A New Perspective

35:51 Lifecycle Marketing: Engaging Existing Customers

39:20 Rethinking Marketing Goals and Metrics

42:39 The Evolution of Marketing Structures

45:02 The Future of Marketing: Innovation and Adaptation 

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Takeaways

• Companies are exploring underutilized marketing channels for 2025.
• Direct mail and gifting are emerging as effective marketing strategies.
• The evolution of Sendoso reflects the need for both sales-led and product-led growth.
• Sales and product-led growth must be balanced for success.

Sound Bites

• "The inbox on LinkedIn is broken."
• "Resumes are almost dead."

Chapters

00:00 Exploring Underutilized Marketing Channels

05:00 The Evolution of Sendoso: From Sales-Led to Product-Led Growth

09:49 Navigating the Challenges of Product Development

13:50 The Importance of Personal Branding in B2B

20:11 The Future of Content Creation and Marketing Strategies

24:39 The Evolving Landscape of Business Growth

25:57 Rethinking Go-to-Market Strategies

27:48 The Renaissance of Employee Education

29:44 Building a Sustainable Outbound Engine

31:10 Balancing Sales and Product-Led Growth

33:20 Navigating Customer Success and Sales Dynamics

35:35 The Future of Account Management

38:26 AI Agents in Customer Interaction

41:43 The Integration of AI in Customer Support

43:37 The Expanding Definition of Go-to-Market

45:31 The Future of Cross-Functional Teams

47:27 The Role of AI in Product Optimization 

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Our five principles of organizational design and how to navigate growth and scaling challenges, particularly in startups.

takeaways

• Growth should be a collective responsibility across all departments.
• High internal conflict is a sign of poor organizational health.
• C-level executives must act as translators between departments. Internal curiosity is as important as external curiosity.
• Smaller companies often scale too quickly without solid foundations.
• Founders should maintain humility about what they don't know.

Sound Bites

• "We start out with a high-level idea, then complicate it."
• "You should measure MQLs, not celebrate them."
• "Make sure you're alive to fight in the next round."

Chapters

00:00 Understanding the Dual Role of a CMO

06:08The Ownership of Growth: A Collective Responsibility

12:12 Organizational Design: Indicators of Health and Conflict

17:51 The Complexity of Metrics and Data Overload

23:56 Cross-Functional Collaboration: The Role of C-Level Executives

30:38 The Importance of Internal Curiosity

31:36 Lessons from the GE Hawthorne Experiments

32:32 Feedback and Communication in Organizations

34:21 Five Principles of Organizational Design

36:14 Designing for Healthy Conflicts

37:40 Rethinking Marketing Qualified Leads (MQLs)

40:02 The Role of Incentives in Organizational Success

42:17 Establishing Fail-Safe Processes

44:13 Challenges Faced by Smaller Companies

45:08 The Need for Humility in Startups

48:57 The Complexity of Large-Scale Projects

50:50 Understanding Time vs. Money in Enterprise Sales

52:00 Practical Advice for Implementing Change

56:41 Managing Big Projects Effectively

59:01 Staying Alive in the Competitive Landscape

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Leah on Linkedin / Twitter / Youtube

The challenges of implementing product-led sales strategies and the importance of simplifying metrics for effective decision-making. Why traditional customer metrics don’t work that well anymore and why it’s all about two things in business, no matter the scale:

Securing and growing customers.

Takeaways

• C-level roles require a focus on company-wide outcomes, not just departmental interests.
• Cross-functional problems often feel dangerous with little upside.
• Sales teams often lack the skills to interpret data effectively.
• Transforming organizations requires a willingness to challenge the status quo.

Sound Bites

• "Revenue happens everywhere."
• "What does good look like?"

Chapters

00:00 Rethinking Sales Models for Modern Business

12:04 The Role of Customer Success in Revenue Generation

24:06 Understanding C-Level Responsibilities and Cross-Functional Collaboration

28:19 Bridging Data Silos in Organizations

32:34 The Challenge of Product-Led Sales

36:47 Simplifying Metrics for Better Decision Making

39:11 Rethinking NPS and Customer Success Metrics

42:56 Time to Value: A Key Metric for Success

46:48 External Benchmarks and Customer Perspectives

49:40 Transforming Organizations for Modern Business

55:50 Closing Thoughts and Future Connections

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Leah on Linkedin / Twitter / Youtube

The evolution of demo technology, the role of Gen.AI in enhancing demo creation, and the shifting dynamics of the sales process towards a more self-service model.

How does the future of marketing in a product-led world look like for Sales?

Takeaways

• Gen.AI will revolutionize demo creation and usage.
• The market for interactive demos is expanding rapidly.
• Buyers prefer to explore products independently before engaging sales.
• Budget holders are becoming more flexible and decentralized.
• Value-driven marketing will replace traditional methods.

Sound Bites

• "Interactive demos are a stepping stone towards PLG."
• "Stop playing with words, play with value."

Chapters

03:57 Defining Interactive Demos

09:46 The Evolution of Demo Technology

14:02 The Impact of Gen.AI on Demos

20:04 The Future of Sales and Interactive Demos

26:05 The Evolving Role of Sellers in Tech Sales

27:05 Changing Dynamics of Budget Holders

28:54The Shift in Market Approach

30:15 The Importance of Market Understanding

32:05 Navigating the Competitive Landscape

33:32 The Power of Buyer Enablement

34:32 The Role of Interactive Demos

36:50 The Future of Interactive Demos

39:22 The Impact of Interactive Demos on Sales

41:13 The Fragmentation of the Interactive Demo Market

44:05 The Integration of Sales and Product Analytics

48:50 The Future of Marketing in a Product-Led World

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What is our pricing strategy for what we do, and how did we come up with it? How does Teresa’s demand generation differ from Marty Cagan's or mine?

takeaways

• Coaching should be a mutual investment of time and resources.
• Not all requests for help are equal; specificity matters.

Sound Bites

• "I charge a speaking fee to protect my energy."
• "Be brief when reaching out for help."

Chapters

01:13 Understanding Introversion in a Social World

04:02 Setting Boundaries: The Challenge of Social Requests

08:15 The Value of Speaking Engagements and Energy Management

12:09 Crafting Effective Requests: The Importance of Specificity

15:27 Navigating the Landscape of Help Requests

20:30 Monetization and Value: Setting the Right Price

30:12 The Evolution of Pricing Strategies

37:19 Final Thoughts: The Importance of Investment in Coaching

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Francesca Cortesi shares with me insights on the difficult journey from finding product market fit to getting to an IPO. We particularly explore the details of Hemnet, a Swedish B2B2C SaaS marketplace and how they dealt with this challenge.

takeaways

• Defending existing revenue becomes a priority as companies scale.
• Diluting your value proposition can occur when scaling too quickly.
• Sustainable growth should be prioritized over rapid expansion.
• Post-market fit requires speed within control and structured decision-making.
• Founders must transition from product-centric to organizational leadership roles.

titles

• From Market Fit to IPO: The Hemnet Journey
• Scaling Strategies for Product Leaders
• Navigating Growth Stages in Tech Companies
• The Role of Innovation in Sustaining Growth

Sound Bites

• "It's a matter of taking down your ego."
• "Don't forget about your core product."

Chapters

04:53 The Journey of Hemnet: From Startup to IPO

09:57 Navigating Company Growth Stages

14:57 The Importance of Innovation Post-IPO

20:09 Challenges of Scaling: CFO and CPO Perspectives

23:53 The Challenges of Scaling and Alignment

27:59 Mindset Shifts for Sustainable Growth

30:18 Navigating Post-Market Fit Dynamics

35:22 The Lottery Win: Managing Growth Expectations

39:34 Focus and Structure: Keys to Avoiding Pitfalls

44:27 B2B2C Dynamics: Balancing Customer Needs

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Leah on Linkedin / Twitter / Youtube

Are multiple income streams and optionality realistic to mitigate the fear of job loss? How does personal career development overlap with product management? The significance of networking and communication skills and the evolving field of AI and how to adapt to it.

takeaways

• 70% of job seekers find opportunities through personal connections.
• It's important to be open and generous in networking efforts.
• Finding personal goals is crucial; not everything is monetizable.
• Continuous learning and adaptation are vital in the tech landscape.

Sound Bites

• "Don't stay in one lane; connect two lanes."

Chapters

12:47 The Importance of Networking and Personal Branding

24:07 Exploring Optionality and Income Streams

26:10 Leveraging Product Management Skills in Diverse Fields

27:09 Finding Personal Goals: Money vs. Joy

28:31 The Importance of Passion in Career Success

30:34 Navigating Career Choices and Social Status

32:54 Building a Career Roadmap: Steps and Strategies

34:23 Overcoming Hurdles: Grit and Resilience in Career

37:18 The Art of Follow-Up: Networking and Communication Skills

41:00 Understanding AI: Getting Started in a New Field

46:28 The Future of AI: Learning and Adapting to Change 

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De-risking strategies to avoid surprises and the significance of celebrating good decision-making processes rather than just successful outcomes. 

Takeaways

• Working autonomously means communicating more, not less.
• Surprises in the workplace are generally unwelcome.
• Celebrate the process of good decision-making, not just results.
• Make your proposals easy for others to present.
• Communication should be proactive, not reactive.

Chapters

01:51 Introduction to Wes Cowell and His Journey

02:51 Obsession vs. Discipline in Achieving Success

06:30 The Art of Executive Communication

07:51 Building Buy-In for Ideas

11:10 The Role of Credibility in Communication

15:24 Understanding Bandwidth in Conversations

19:34 Framing Conversations for Clarity

22:22 Reducing Cognitive Load in Communication

27:31 Cross-Functional Communication Strategies

30:51 Effective Communication in Leadership

34:06 De-risking Proposals and Feedback Loops

39:38 Celebrating Good Decisions Over Results

44:10 The Importance of Rigorous Thinking

54:30 Preparing Others for Success in Presentations

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We explore effective onboarding strategies, the importance of aligning customer success with product development, and the necessity of quantifying challenges faced by customer success teams.

What’s the importance of defining effective KPIs for customer success, focusing on leading indicators rather than lagging ones? How DO we measure customer happiness? Is the NPS as useless as I believe it is?

takeaways

• Onboarding strategies must focus on delivering value quickly by measuring time to value.
• Consultative approaches to customer success add significant value.
• Customer success teams often act as advocates for product improvements.
• Focus on leading indicators for customer success.
• Customer segmentation should be based on use cases, not just size.

Chapters

04:45 Understanding Customer Success and Onboarding Strategies

09:48 The Role of Customer Success in Product Development

14:50 Bridging the Gap Between Customer Success and Product Teams

19:56 Quantifying Customer Success Challenges and Solutions

23:41 Understanding Product Impact on Business Metrics

28:19 Defining Effective KPIs for Customer Success

33:06 Measuring Customer Engagement and Value

38:07 The Myth of Customer Happiness

43:11 Data-Driven vs. Data-Informed Decisions

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How to embrace your vulnerabilities and the importance of leaving a positive impression in sales interactions while getting insights you would never get just by looking at data.

How to balance product-led growth with effective sales strategies before its too late.

takeaways

• Sales can be enjoyable once you find your own style.
• Calculated risks in entrepreneurship are often misunderstood as reckless.
• Product-led growth can coexist with sales-led strategies.
• The definition of product growth is evolving. Founder-led sales is crucial for early-stage startups.
• Hiring salespeople too early can be risky.

Sound Bites

• "I learned to enjoy sales."
• "Entrepreneurship is not as risky as it seems."
• "You cannot hurry your clients."
• "Sales is about refining the ICP and messaging."
• "Product-led growth is about cost efficiency."

Chapters

03:09 Understanding Risk in Entrepreneurship

05:59 The Psychology of Product Development

08:48 Balancing Product-Led and Sales-Led Approaches

12:06 Navigating Early Sales Challenges

14:52 The Importance of Customer Retention

18:11 Building a Product That Sells Itself

21:00 The Role of Paid Pilots in Sales

23:57 Leaving a Lasting Impression in Sales

27:36 The Power of Founder-Led Sales

30:26 Misconceptions About Sales and Selling Styles

33:16 The Importance of Personal Sales Experience

36:19 Leveraging Sales Insights for Product Development

43:01 Refining Messaging and Understanding Customer Expectations

48:03 Balancing Product-Led Growth and Sales Strategies

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Why the traditional role is shifting to a more integrated approach and how this works when “the sale never ends”

We discuss the complexities of customer success, the impact of budget constraints on customer retention, and the importance of understanding customer churn.

What it means to build around mission-critical services and having the correct timing to introduce customer success to a company. How does sales compensation integrate with customer success actions and how can we transition customers smooth between sales and customer success?

What do “Head of” titles mean if anything?

Without a doubt one of my favorite episodes I have ever recorded.

takeaways

• The role of customer success is evolving to include revenue ownership.
• Customer success can be seen as an extension of sales but with a different approach.
• The sale never truly ends; it's an ongoing relationship.
• Customer success leaders need to demonstrate their impact on revenue.
• Customer success should be integrated into product development.
• Sales compensation should align with customer success goals.

Sound Bites

• "Own revenue outcomes."
• "The sale never ends."
• "A ‘head of’ is a lawyer for their function."

Chapters

06:46 The Evolution of Customer Success

13:48 Revenue Ownership in Customer Success

19:57 The NPS Debate: Metrics and Insights

28:21 Understanding Customer Churn and Budget Constraints

31:08 The Role of Customer Success in B2B SaaS

33:59 When to Introduce Customer Success Management

36:14 Sales Compensation and Customer Success Integration

39:37 The Importance of Smooth Handoffs in Customer Success

40:34 Connecting Product Usage Data to Sales

45:22 Navigating Titles: Head of vs. VP in Organizations

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Leah on Linkedin / Twitter / Youtube

Why is everyone suddenly providing a pipeline from product, marketing, sales, and customer success while the only way that most companies measure pipeline is through Marketing and their MQLs (Marketing Qualified Leads)? Why does this old model not work anymore?

takeaways

• Demand comes from various sources, but visibility is lacking.
• MQLs are often an arbitrary measure of lead quality.
• Valuations in the market are not always reflective of true value.
• Building a sustainable company requires a focus on customer conversion. MQLs often lead to inefficient marketing practices.

Sound Bites

• "There's very little visibility into what's actually working."
• "MQLs are an arbitrary definition of leads."
• "It's very spray and pray-oriented."

Chapters

04:56 The Evolution of Growth Strategies

10:01 The Dichotomy of Product-Led and Sales-Led Growth

15:05 The Importance of Founders and Team Dynamics

19:54 The Future of CRM and Data Integration

25:07 Rethinking MQLs and Sales Incentives

27:30 Rethinking MQLs: A New Approach to Marketing

30:55 Defining Success: The Role of ICPs in MQLs

34:41 The Interplay of Marketing, Sales, and Customer Success

39:42 Navigating Customer Journeys: The Role of Support

44:03 The Future of Investment: AI and Market Dynamics

49:10 The Evolution of Inbound Marketing: Finding New Channels

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Leah on Linkedin / Twitter / Youtube

How do you train this muscle? And where do memes fit into our dry tech industry? Why is building a brand such a painful experience due to the needed consistency,

Interview conducted by Vincent Pierri 🙏 (Public Speaking Voice Coach), who offered his time to generously donate his time to turn me into a guest for once about a topic I don’t specifically talk about.

Takeaways

• Different audience sizes require different speaking strategies.
• Feedback loops are essential for improving public speaking skills.
• Humor can be a powerful tool in public speaking.
• Consistency is key in building an online presence.
• Having a unique point of view is essential for engagement.
• Rising recognition can lead to a more isolated experience.

Sound Bites

• "Public speaking is not just in the public."
• "You should not be a senior leader if you cannot speak well."

Chapters

02:45 The Journey into Public Speaking

09:11 The Importance of Content and Delivery

12:00 Navigating Different Audience Sizes

14:53 The Role of Feedback in Public Speaking

18:10 The ROI of Public Speaking for Tech Leaders

20:52 Crafting Effective Presentations

26:52 Gary: The Memorable Character from Sales

29:50 Preparing for Talks and Finding Your Voice

38:14 The Value of Podcasting

42:02 Navigating LinkedIn for Audience Building

47:01 The Pain of Personal Branding

51:49 The Journey of a D-List Celebrity 

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Leah on Linkedin / Twitter / Youtube

The complexities of navigating the B2B sales landscape suddenly after selling to individuals.

takeaways

• “The core concept was how can we get people to do something for less than three minutes a day around their finances.”
• The shift from B2C to B2B requires different strategies.
• Internal tools often fail to meet market needs.
• Navigating the complexities of B2B sales is a learning process.

Chapters

06:00 Innovative Approaches to Financial Health

11:48 Engagement Strategies in Fintech

18:12 The Human Connection in Financial Services

24:06 Building a Sustainable Business Model

27:22 Financial Stress and Mental Health Nexus

30:39 Challenges in Internal Tooling for HR

32:31 Pivoting from B2C to B2B Strategies

36:03 Data-Driven Insights for HR

40:56 Navigating the B2B Sales Landscape 

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Her concept of a vision is, to me, one of the very few that I think is actually cutting through the noise and has an impact aside from the cookie-cutter frameworks we had so far.

It’s beyond processes over mere goal-setting in achieving long-term success in startups.

takeaways

• Pivots should be treated as silver bullets, used deliberately.
• A strong vision can save not just a product line but also sanity.
• Innovation should not be sacrificed for optimization.
• Processes should be prioritized over mere goal-setting for better outcomes.

Chapters

17:28 The Importance of Vision in Startups

36:54 Aligning Teams Through Vision and Strategy

51:26 Balancing Innovation and Optimization

01:02:17 The Role of Processes Over Goals

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Leah on Linkedin / Twitter / Youtube

What’s the difference between really good leaders and bad managers?

Takeaways

• Change management should simplify processes, not complicate them
• Workplace dynamics are influenced by external advice.
• Hiring should focus on long-term vision and fit.
• Leadership requires balancing urgency with pragmatism.

Sound Bites

• "People are getting too much of their work advice from TikTok."

Chapters

02:55 The Art of Direct Communication

05:50 Navigating Workplace Dynamics

09:07 Building Trust in Teams

11:55 The Evolution of Work Structures

14:48 Effective Team Management

18:05 The Importance of Clarity in Roles

24:04 Hiring for the Future

26:54 The Role of Leadership in Change

30:01 The Challenge of Executive Hiring

33:13 The Impact of AI on Recruitment

36:02 Networking in Today's Job Market

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Leah on Linkedin / Twitter / Youtube

Data in product management, the limitations of traditional tools, and the future of product management with AI. 

Takeaways

• Founders often struggle with letting go of control.
• Micromanagement can be necessary but should be balanced with empowerment.
• Traditional product management tools often fall short in meeting modern needs.
• AI will transform the way product management operates.
• Unshipping features is essential for product evolution.

Sound Bites

• "Ego should really never play a role here."
• "I never make any decisions here alone."
• "There's nobody more incentivized to make this whole thing work than the founders."

Chapters

03:12 The Journey of AirFocus

05:59 Navigating Founder Mode and Micromanagement

09:13 Balancing Control and Empowerment

11:59 The Role of Data in Product Management

14:53 Challenges of Traditional Product Management Tools

18:03 The Future of Product Management with AI

20:55 Empowering Engineers in Product Development

23:49 Unshipping Features and Product Evolution

27:03 Connecting Sales and Product Management

29:51 The Importance of Customer Insights

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Leah on Linkedin / Twitter / Youtube

The branding experts Shannon Deep and Kevin Lee dig into exploring the multifaceted nature of brand measurement and strategy.

Misconceptions surrounding brands and risks associated with brand decisions, the importance of aligning brand strategy with business goals, and the challenges faced by founder-led brands in maintaining their identity.

What does marketing look like in the future? Where does product marketing sit?

Takeaways

• Many senior leaders conflate brand with just design and visuals.
• Brand is an additional filtering mechanism for attracting the right customers.
• Measuring brand effectiveness can be complex but is crucial for growth.
• Founder-led brands face unique challenges in separating their identity from the company.
• Brand marketing is becoming increasingly important in the current business landscape.
• You can measure brand through various metrics, including share of search and brand awareness.

Sound Bites

• "Brand is the sum total of all experiences."

Chapters

07:31 Understanding Brand Beyond Visuals

14:41 Navigating Brand Decisions and Risks

22:46 The Role of Brand in Business Strategy

30:43 Measuring Brand Effectiveness

37:28 The Challenge of Founder-Led Brands

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Leah on Linkedin / Twitter / Youtube

How to build a strong bench of performers, balancing authenticity and urgency. How do you make yourself care about boring topics and find joy in work?

Why feedback loops and building team connections become more important as an organization scales. How do we deal with weak performers, skip-level meetings, and when to invest in strong performers?

Why growing others is always paying dividends and make you more secure.

Takeaways

• Balancing authenticity and urgency is a challenge in leadership, but it is important to be true to oneself while maintaining a sense of urgency.
• Transitioning from an operative role to a product leadership role involves a shift in power dynamics and the need to build connections with team members.
• Managing weak performers can be challenging, but it's important to depersonalize the conversation and focus on finding the right match for the role.
• Skip-level meetings provide unique insights and opportunities for career development.
• Generosity and supporting others in their growth are key qualities of a secure leader.

Sound Bites

• "Invest in what you think the future looks like"
• "Recognize and address mistakes, then move forward"
• "What I do like is like calling everyone on the phone and saying like, 'How are you? What's going on with your career? What can I help with?'"

Chapters

00:00 Investing in the Future: Building a Strong Bench

06:03 Balancing Authenticity and Urgency in Leadership

08:19 Forgiving Oneself: Learning from Mistakes

18:13 Finding Motivation: Understanding Why

25:08 Building Connections: Fostering Unity in Scaled Organizations

26:03 Navigating the Shift in Power Dynamics

27:28 Building Connections through One-on-One Conversations

28:55 The Importance of a Growth Mindset and Feedback

31:20 Managing Weak Performers with Empathy

32:17 The Role of Skip-Level Meetings

34:07 Investing in Strong Performers for the Future

36:27 The Power of Generosity in Leadership 

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Leah on Linkedin / Twitter / Youtube

I talked with Austin on the rise of superficial marketing tactics and what they do to the importance of building a strong brand.

We discuss why Product Managers cannot ignore Marketing anymore and the value of good dogfooding in product development when everyone tells you to “listen to your customer”.

How to transition from being your own ideal customer to targeting a different market segment.

Takeaways

• Marketing is moving from a deterministic approach to a more probabilistic approach, where marketers have less control and understanding of who and how to reach people.
• The rise of superficial and cringe-worthy marketing tactics on platforms like LinkedIn is a result of increased competition and the need to stand out.
• Traditional CRMs have limitations in terms of speed, data entry, and automation.

Sound Bites

• "Marketing is moving back to the ways things were done in the 1960s to the 1990s, where you're not going to have as much control and understanding about who and how to reach people."
• "We're just shifting market shares around without deriving value to the customer."
• "You can be a really good dog fooder of your product, but you may not be the ideal ICP for your product in the future."
• "The core product is never done. Whenever you add something else, it becomes a little bit worse, and then you need to repatch it up."

Chapters

08:12 The Rise of Superficial and Cringe-Worthy Marketing Tactics

13:55 The Importance of Building a Strong Brand

23:40 The Role of Marketing in Product Development

29:03 The Value of Dogfooding in Product Development

31:25 The Value and Challenges of Dogfooding

38:12 The Never-Ending Process of Product Development

39:07 Balancing Customer Feedback and Vision

53:46 The Limitations of Traditional CRMs

01:00:15 Introducing Clarify: Disrupting the CRM Market 

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Leah on Linkedin / Twitter / Youtube

Rand Fishkin and me discuss the challenges and limitations of paid advertising, the role of AI in marketing, the importance of organic initiatives and why you can’t skip good quality audience research.

Takeaways

• Many marketers spend money on ads that are shown to people who would have converted anyway.
• The best marketing channels are often the hardest to measure. Paid advertising can be limited and may not always provide the desired results because you don’t see how they really perform.

Sound Bites

• "There's lots of people being taken advantage of in the digital marketing and advertising ecosystem today."
• "There are literally hundreds of billions of dollars that flow into that ecosystem that don't necessarily have careful accounting."
• "We're going to need to do these sketchy things that essentially take credit for sales that would have already happened, show people more ad results, reduce the quality of the organic results, make it harder to identify ads, force people to scroll down further, lazy load the organic stuff and quick load the paid stuff."
• "Treat digital advertising the way Coca-Cola treated billboards in 1965. Test different messages and campaigns in specific markets and analyze the lift in same-store sales to determine effectiveness."

Chapters

06:30 The Issues with Digital Advertising

10:22 Taking Advantage of the Digital Marketing Ecosystem

13:14 The Challenge of Proper Accounting and Attribution

18:29 The Misleading Nature of Digital Metrics

23:03 The Difficulty of Measuring the Best Marketing Channels

23:59 The Limitations of Paid Advertising and the Need for Innovation

25:27 The Impact of AI on Marketing and the Changing Web

28:10 The Value of Organic Initiatives in Marketing

29:31 Testing and Experimentation in Marketing

34:13 The Importance of Working with Competent Experts

41:26 The Significance of Qualitative Metrics in Marketing

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Leah on Linkedin / Twitter / Youtube

We discuss different mental models for how different functions work together as teams and why it’s important to clarify and document the operating model, especially during times of growth, turnover, or changing strategies.

John talks about the concept of scaffolding is introduced as a way to navigate the process of change and improvement and why most crossfunctional initiatives fail.

Takeaways

• Define in an operating model team sizes, roles, and responsibilities
• Reduce single points of failure and promote shared accountability
• Establish a shared language around team and domain evolution
• Stay firm on the chosen operating model and evaluate it within a specific timeframe

Sound Bites

• "We invest in teams, products, and outcomes, not individual projects and deliverables."
• "What are the valid reasons to ask for money and what kind of rigor are you going to put for them for their team?"
• "Teams respond well if there are a small number of things that people are stubborn about."

Chapters

06:45 The Need for an Operating Model in a Growing Company

08:04 Running a Collaborative Product Organization

14:32 The Challenges of the CPO and CTO Tandem

19:26 The Importance of Clarifying and Documenting the Operating Model

29:00 Scaffolding and Navigating Change

38:23 Team Size and Misalignment in SaaS Teams

39:18 Investing in Teams, Products, and Outcomes

41:27 Valid Reasons to Ask for Money and Team Rigor

45:03 The Importance of Being Stubborn

46:46 The Power of Enable Constraints

51:54 Defining Team Sizes and Roles

01:05:30 The Role of Engineering Managers in Teams

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Leah on Linkedin / Twitter / Youtube

Pedro Góes, the founder and CEO of InEvent, discusses with me the challenges and strategies of selling to enterprise clients in the event tech industry.

Why in-person interactions and relationship-building can’t be beat by pure self-serve. The value of certifications and how they contribute to higher retention rates.

He shares insights on the event tech market, the role of AI in their product, and the differences between doing business in the US and Europe.

Takeaways

• In-person interactions and relationship-building are important for establishing trust and are not just limited to sales.
• Expanding in-person operations and support can be a key differentiator.
• The challenges and regulations of doing business in Europe and the US differ.
• Finding a niche and focusing on a specific market segment can lead to success in an oversaturated market.

Sound Bites

• "We have been trying to focus on this type of clients because it's better retention."
• "We have been building this for 12 years and it's not ready yet."

Chapters

04:43 The Value of Certifications

09:48 Challenges and Opportunities in Enterprise Sales

18:07 Focusing on Key Product Offerings

23:30 The Importance of In-Person Interactions

28:41 Overcoming Sales Challenges

32:30 Expanding In-Person Operations

39:30 Navigating the European and US Markets

42:21 Conclusion

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Leah on Linkedin / Twitter / Youtube

Janna Bastow, CEO & Co-Founder ProdPad / Co-Founder of Mind the Product, shares her perspective on how AI is just another tool that can help product managers synthesize feedback and speed up certain aspects of their job.

Why AI should not replace the human element of product management, such as getting alignment from stakeholders and gathering feedback from real users and how we can think about evaluating roadmaps when they all look the same.

Why product managers being skilled in asking the right questions and validating their ideas with real customers is not optional anymore.

Takeaways

• The value of a roadmap lies in the roadmapping process, not just the document itself.
• AI can be used as a sense checker and sidekick to provide feedback and support decision-making, but human judgment is still crucial. Creating a company culture where employees feel comfortable challenging ideas is crucial for innovation and growth.
• Product managers need to understand how their work connects to revenue and develop roadmaps that align with the company's strategy.

Sound Bites

• "The job of a product manager is to get out of the building and understand what users and the market want. Especially with AI being around"
• "Nobody's getting fired for using AI."
• "Product managers who do not understand how their work connects to revenue will be in trouble in the future."

Chapters

00:00 The Role of Product Managers in the Age of AI

09:08 AI as a Tool for Feedback Synthesis and Speeding Up Product Management

23:17 Human Judgment and Decision-Making in Evaluating Roadmaps

25:34 Creating a Culture of Innovation and Openness

26:22 The Role of Product Managers in Driving Growth

27:41 The Impact of AI on Product Management

32:26 The Importance of Asking the Right Questions

35:19 Adapting to the Changing Landscape of Product Management

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Do PM’s really need to have a basic understanding of data and how it is stored and analyzed with LLMs being the norm? Why business intelligence (BI) tools are not the answer. 

Which key metrics and questions are correct to start with if you’re trying to get your data under control?

Takeaways

• PLG is not suitable for every business
• Business intelligence (BI) tools are good for consumption and reporting, but not for analysis.
• Data quality is a challenge, and engineers need to care about data and be involved in tracking.

Sound Bites

• "There's no best practices the way there are in other fields. Like it's all being written. It's all first principles."
• "There's plenty of businesses that can monetize much better and grow much better focusing on a different segment of the market where PLG isn't the appropriate sales motion."
• "Core root analysis, just following people around this is very, very underappreciated."
• "BI tools are good at consumption. It's good when you've predefined a set of metrics and dimensions and you want to push that out for general consumption."
• "Reporting is great to just keep a pulse on things, but nobody ever found an insight from reporting or nobody ever found something that's needle moving from a report."

Chapters

03:23 The Relevance and Overrating of Product-Led Growth (PLG)

05:15 Finding the Right Sales Motion for Your Business

09:28 The Importance of Tracking and Analytics in Sales Motions

13:44 Focusing on Churn and Retention for Sustainable Growth

22:14 Understanding the First Week Experience and Power Users

26:27 Understanding Data in Product Management

27:52 Limitations of BI Tools

29:19 Challenges of Data Quality and the Need for Engineers to Care

31:44 The Role of the CTO and CPO in Driving Data-Driven Decision-Making

46:34 Getting Started with Data Analysis: Focusing on Key Metrics

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Kyle Pursell, the Head of Growth Optimization at Shopify, talks about impactful business strategies for growth.

What is the challenge of moving upmarket, and the role of product-led growth in driving this success. And why cross-functional collaboration in growth initiatives is often undervalued.

We also talk about the different paths to getting into growth roles and share their favorite podcasts and books.

Takeaways

• Building alignment and getting feedback before important meetings is never optional.
• Cross-functional collaboration is essential for effective growth initiatives
• Focus on maximizing user engagement in the first session to drive activation
• Implement strategies to retain customers who are canceling, such as offering compromises
• Consider different paths to getting into growth roles, such as starting in customer service or marketing

Sound Bites

• "Growth is not an overcomplicated craft. It's just identifying levers, using data to make decisions, experiment."
• "The aim of important meetings like that are just like a rubber stamp. Everyone is aligned."
• "Do not go into a meeting that is important to you without knowing how it ends."
• "Drive people as far down the funnel as possible in that first session as early as possible."

Chapters

07:01 Understanding GMV and Leveraging Metrics

14:28 The Power of Product-Led Growth

28:19 Optimizing Site Speed for Engagement and Conversion

32:10 The Importance of Cross-Functional Collaboration

35:30 The Importance of Stakeholder Alignment in Meetings

38:22 Maximizing User Engagement in the First Session

39:20 Strategies for Retaining Customers Who Are Canceling

51:34 Different Paths to Getting into Growth Roles

01:03:49 Unwinding with Podcasts and Books Outside of Your Field

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In the second conversation with Kieran Flanagan, SVP Marketing at Hubspot we talk about how we see AI really being used in tech and not just being a flashy thing you use once. From Sales, to Marketing to Product. Where are we today and where is all of this going?

The conversation explores the role of AI in strategy, the potential for AI-driven social networks, the impact of AI on user interfaces and customer service, the importance of data in AI tools, and the need for iterative refinement when using AI.

Takeaways

• AI can assist in strategy, but it requires human knowledge and the ability to ask for specific output.
• AI can improve user interfaces and customer service, but there is a risk of increased isolation and loneliness.
• Marketers and business leaders need to have a deep understanding of their own business before leveraging AI. 
• Challenges and limitations of AI include the need for large datasets and the resistance to adopting new software in sales.

Sound Bites

• "It’s not that AI cannot do strategy. You can't do strategy. You don't actually know how to talk to the AI and give it instructions in a way that would actually be helpful towards building a strategy."
• "AI can do a better job than nothing for people who are missing companionship, for people who feel like they are isolated, for people who just crave someone to be there at all times and talk to."
• "You give AI context, you teach it what good looks like before you use it productively."

Chapters

03:04 The Potential for AI-Driven Social Networks

05:59 AI and the Evolution of User Interfaces and Customer Service

08:52 The Importance of Data in AI Tools

14:17 The Limitations of AI in Understanding Context and Reasoning

31:12 Optimizing Workflows and Efficiency with AI

34:28 Enhancing Lead Generation and Conversion with AI

38:41 Improving the Customer Onboarding Experience with AI

44:26 Challenges and Limitations of AI in Sales

50:38 Using AI to Solve Real Problems and Create Value

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I talked with the amazing Andrew Ettinger from Appen about community-led growth in enterprise sales, the importance of cross-functional understanding, and the transformation of content and community in the sales process. 

We are also diving into the impact of AI on the industry and the need for cross-functional understanding and collaboration.

Takeaways

• Cross-functional understanding and collaboration between CROs, CPOs, and other leaders is crucial for successful sales strategies.
• The evolving role of lead scoring and product usage in sales
• The changing nature of sales and product management in the era of AI and automation

Sound Bites

• "Fundamentally, it doesn't matter what you sell. The way in which you need to generate demand is by building out content and value added interactions with the personas that your product or service can enable them to have a 10X better life."
• "If you provide enough high value and relevant content, what you're actually going to find is your form fills get much more detailed about the project."
• "We actually want to talk to all of these people because we learn and we wind up actually doing some projects, even at cost."

Chapters

00:00 Navigating the Challenges of Closing Deals in Modern Sales

05:23 The Role of Community-Led Growth in Enterprise Sales

08:12 Cross-Functional Understanding and Collaboration in Sales Strategies

16:30 Understanding Product-Market Fit in Modern Sales

26:29 The Impact of Data on Sales and Lead Generation

29:43 Evolving Role of Lead Scoring and Product Usage in Sales

31:33 Challenges and Opportunities of Inbound Leads and PLG

32:58 The Importance of Firmographics and Product Usage in Separating Leads

34:21 The Changing Nature of Sales and Product Management in the Era of AI and Automation

42:31 The Need for Cross-Functional Understanding and Collaboration in the Industry

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Jam.dev created a tool called Jam that helps product managers and engineers communicate and debug bugs more effectively. The company has grown to over 100,000 users and has fixed more than 2 million bugs.

They have adopted a unique approach to marketing, prioritizing community building and sharing their journey as builders. The company uses an R&D framework to evaluate and measure the success of their marketing initiatives.

I’m talking with Dany Grant about why it’s not just optional to be close to users in a product-led growth startup and why in-person interactions might matter more than you think.

Takeaways

• Jam.dev prioritizes community building and sharing their journey as builders to connect with their target audience.
• They use an R&D framework to evaluate and measure the success of their marketing efforts. 

Sound Bites

• "When you're a PLG company, the thing that's existential is are you giving value to your users."
• "We sometimes have this really weird thing with PLG companies that we just do not know who we're talking to because we do not foster this kind of real-life connection."
• "Even if we do not generate leads and money from the actual events, you kind of still do because you get information about who it is that is buying your stuff."

Chapters

03:51 Innovative Bug Reporting and Communication

08:13 Marketing Strategies: In-Person Events and Social Media

23:58 Being Close to Users in a PLG Startup

26:30 Understanding User Connections in PLG

27:54 Gaining Insights from Events and User Interactions

31:12 Struggles with Identifying the Ideal Customer Profile (ICP)

33:30 Onboarding Larger Companies through Smaller Teams

38:13 The Journey of Building a Startup and Team Growth

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Burnout and the pursuit of external validation in tech. 

The pressure to constantly achieve and the belief that success will bring happiness and fulfillment is driving some of us into ruin. It almost did with Andy Johns, he was never more successful and unhappier in his life until he his body hit the reset switch.

Top companies, top jobs, top titles. Achieve, achieve, achieve. And yet it’s never enough… A lot of us are chasing external validation so we don’t have to deal with and accept ourselves.

Takeaways

• The tech industry, with its emphasis on high performance and success, often perpetuates the cycle of burnout.
• Removing the masks we wear and being vulnerable with others is important for personal growth.
• Letting out suppressed emotions and desires is a crucial step towards healing and finding our true selves.

Sound Bites

• "The human superpower is the ability to imagine things that aren't real."
• "Not everyone who's succeeding, at least on paper, is doing as well on the inside as they are on the outside."
• "I was seeking something external to myself that would make me feel lovable, whole, and complete."

Chapters

03:42 The Pressure to Achieve and the Illusion of Happiness

09:56 The Importance of Self-Love and Addressing Traumas

15:45 The Tech Industry and the Cycle of Burnout

33:42 The Limitations of Free Will

37:35 Losing Touch with Our Authentic Selves

42:52 Strength in Vulnerability

57:03 Regretting the Delay in Self-Discovery

01:02:11 Depression as a Result of Suppression

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He explains the power of organic reach through LinkedIn and building a personal brand through social media, particularly LinkedIn, and how important it is to not be too rigid in your assumptions. Adam shares his experience with video content and its impact on building trust and affinity with his audience to sell and scale an impressive B2B product-led flywheel.

We talk about the concept of freemium product-led growth (PLG), the value of free users, and why it’s worth it to keep them around, even if they never buy.

Takeaways

• Building a personal brand through organic reach on social media platforms like LinkedIn can create trust and affinity with the audience, especially in B2B.
• Video content allows for a richer and more dynamic connection with the audience, enhancing the impact of your brand.
• Retaining free users is valuable for organic distribution and building domain authority.
• The combination of AI and influencer-type founders can enable bootstrapped startups to scale and compete with larger companies. We are just at the beginning.
• Point solution products with a massive free offer and a focus on viral expansion can disrupt traditional SaaS models.

Sound Bites

• "I want to challenge myself to just keep adding value to the paid plan until we get decent conversion rates instead of taking value away from the free one."
• "I think video builds an affinity for you in a way that nothing else can because people are sitting there, they're observing your mannerisms and the way that you say things and like the sound of your voice and everything."
• "No user is a free user. You get something from everyone."

Chapters

02:16 The Impact of Video Content on Building Trust and Affinity

08:45 Understanding Customer Churn and Market Dynamics

23:38 The Value of Offering a Free Product to Build Brand Presence

24:07 Freemium PLG and the Actual Value of Free Users

25:37 What can and should you “automate” about personal connections?

33:00 The Importance of Retaining Free Users

35:26 The Future of AI and Bootstrapping, hyper-efficiency

Adam's LinkedIn: https://www.linkedin.com/in/retentionadam/

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Summary

We talk about how to approach Email, how to use it from the ground up to drive meaningful business and how to measure it. How to balance different channels, such as influencers, podcasts, and newsletters.

What IS good content and should you repurpose it? What is the difference between a Short-term and long-term goal, when to drop money into Ads vs. the quality of the content?

We talk about engagement metrics and validation points, how to encourage an open structure for content posting, tracking engagement metrics and pipeline opportunities, the long-term play and how to trust in a B2B content strategy, separating reporting for different content types, gathering information and filtering leads, and choosing the most valuable question to ask.

Takeaways

• Email marketing is still a valuable channel for demand generation despite the flood of automation and AI, but it requires targeted goals and effective use.
• Create good content that is valuable to a specific audience and consider repurposing content to maximize impact.
• Set short-term and long-term goals for growth, and use benchmarks to guide your strategies.
• Gating content in newsletters should be done sparingly, as building trust and showcasing content upfront are more important than gathering low-intent emails.
• Separate reporting for different content types to accurately evaluate performance.

Chapters

04:22 The Importance of Email in Demand Generation

10:56 Creating Good Content for a Specific Audience

13:38 Repurposing Content and Optimizing Channels

16:29 Short-Term and Long-Term Goals for Growth

21:46 Setting Targets and Benchmarks for Growth

24:06 Importance of Quality and Amplification in Newsletters

26:27 Gating Content in Newsletters

29:10 Differentiating Friction Based on Buying Intent

30:38 The Five Degrees of Content

35:18 Engagement Metrics and Validation Points

39:33 Tracking Engagement Metrics and Pipeline Opportunities

40:28 Long-Term Play and Trust in B2B Content Strategy

41:26 Separating Reporting for Different Content Types

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Summary
Intuition and hiring is an uncomfortable topic. We should be rational, have reasons for why we choose to work with someone or not. When should we trust our gut feeling? When is it time to step back and say, no. I go with the hard facts?

In the end it’s all about building an honest relationship as a leader with our peers and what kind of person you want to be. Afterall, we spend a huge time with our peers, even if work is not our main focus in life.

We explore the journey of personal growth and learning, the challenges and strengths of introversion and extroversion, and the significance of choosing battles and seeking feedback.

How can we understand ourselfes better and become the inspiring leaders that we wish we had in our life when we were younger?

Takeaways

• Intuition and logic are both valuable in decision-making, and it is important to know when to choose which one.
• We don’t have to be leaders by embracing the bad stereotypes from the past.
• Clear communication and honesty are essential in building strong relationships.
• Taking risks and embracing vulnerability will lead to personal growth and learning.

Chapters

05:01 The Power of Clear Communication

07:13 Balancing Simplicity and Complexity in Writing

08:12 The Importance of Honesty in Relationships

14:25 The Wisdom of Intuition and Logic

23:00 Building Honest and Deep Relationships with your peers

26:17 Personal Growth and Learning

29:32 Navigating Introversion and Extroversion

32:59 Overcoming Fear and Embracing Authenticity

38:05 Inspiring Others and Building Meaningful Relationships

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Peter Walker, Head of Data Insights at Carta discusses with me various aspects of startup funding and investment. We explore the value of small angel investments, the obscurity of startup funding letters, the selectivity of startup advisors, and the potential of angel investments as marketing assets.
We also touch on the excitement for the future of startups, the impact of accelerators and venture studios, and the importance of distribution and growth and whether a downround really is such a bad thing.

Takeaways

• There is a growing trend of companies exploring non-VC growth paths and aiming to achieve venture-scale outcomes without raising additional funding.
• The use of startup funding letters, such as Series A and Series B, can obscure the wide variation in funding amounts and create unnecessary pressure for founders.
• Angel investments can serve as marketing assets for startups, as investors with a strong brand can enhance a company's image.
• The current generation of startups is building on a higher foundation of knowledge and asking different questions compared to previous years.

Chapters

13:35 The Shift Towards Non-VC Growth Paths

25:24 The Impact of Liquidation Preferences and Equity Education

43:52 The Value of Small Angel Investments

44:50 The Obscurity of Startup Funding Letters

46:14 Angel Investments as Marketing Assets

48:02 Excitement for the Future of Startups, Accelerators and Venture Studios

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As the CEO of a banking service that focuses on the impact of cashflow mismanagement on small businesses, he knows what it means when people only focus on what’s fun to them in a business and the price they pay for that.

We talked about the decision to seek VC funding and how he built resilience and dealt with negative emotions in tough times. What it means to him to deliver more value than just being a banking app by building out new channels like a podcast.

Takeaways

• Ruthless prioritization is crucial for productivity and success.
• Cashflow mismanagement is a major problem for small businesses.
• Recognize that negative emotions often feel worse and last longer than they are.
• Creating valuable content and delivering practical knowledge can help businesses establish trust and attract customers.
• Focus on quality rather than quantity in marketing to ensure relevance and engagement.

Timestamps

03:18 The Problem of Cashflow Illiteracy in Small Businesses
07:58 The Habit of Writing Down Priorities and ruthless prioritization
15:03 Mismanagement of unfun tasks in Small Businesses
19:37 The Challenges of Financial Management in Early Stages
23:08 The Decision to Seek VC Funding
32:34 The Importance of Effort and Determination
38:01 The Problem of Comparing Self to Others
42:09 Balancing Stressful Situations
46:27 Managing Negative Emotions
48:58 Starting a Podcast and delivering extended value to customers
56:36 Quality over Quantity in Marketing

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How do you set outcome-driven goals for exploratory research and the role of humility in organizational success? Why shipping something does not mean you’re adding value.
Finally, we discuss common failure points in organizations and the future of impactful startups.

Takeaways

• Executives should practice humility and accountability, admitting when they are wrong proactively.
• Setting outcome-driven goals for exploratory research helps determine the value and feasibility of new ideas.
• Common failure points in organizations include a lack of humility, a failure to prioritize the customer, and an overemphasis on the next hottest thing.

Timestamps

00:00 The Power of Humility and Accountability

13:06 The Importance of Putting the Customer First

19:08 Avoiding the Overuse of AI

25:46 Setting Outcome-Driven Goals for Exploratory Research

32:31 The Role of Humility in Organizational Success

43:39 Common Failure Points in Organizations

45:24 The Future of Impactful Startups

Shownotes

Jeff Gothelf: https://www.linkedin.com/in/gothelf/

Jeff’s Website: https://jeffgothelf.com/

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Melissa Kwan, CEO of eWebinar and serial bootstrapper, discusses the challenges and benefits of bootstrapping a business versus seeking venture capital funding. She is the poster child for urging founders to focus on real customer feedback and paying customers without loading up on VC problems. 

We discuss the importance of understanding the customer, personal goals and ambitions, the challenges of building and scaling a product, defining success and financial goals, the desire for financial independence, determining the financial number to sleep well, and the value of personal branding and trust.

Takeaways

• Bootstrapping is a lifestyle choice that offers freedom and control over the direction of a business. At the same time, venture capital funding commits a company to a venture-scale outcome and a different lifestyle.
• The future of tech startups lies in vertical SaaS businesses and smaller, niche solutions that cater to specific markets.
• Why demo calls and salespeople are becoming less necessary as self-serve options and efficient onboarding processes become more prevalent.
• Determining the financial number needed to sleep well varies for each individual.
• Personal branding and trust are valuable assets for entrepreneurs.
• Writing and building an audience can lead to new opportunities and connections.

Timestamps

00:00 The Lifestyle Choice of Bootstrapping vs. VC Funding

05:17 The Trajectory of eWebinar's Growth

09:31 The Challenges of VC Funding and the Importance of Profitability

13:51 The Difference Between Media Validation and Market Validation

19:35 The Rise of Vertical SaaS and Lifestyle Businesses

25:46 The Importance of Analyzing Past Behavior to Predict Future Behavior

32:00 The Problem with Demo Calls and the Shift Towards Self-Serve

37:06 Determining Pricing and the Value of Respecting Customer's Time

45:27 Understanding the Importance of Knowing the Customer

46:25 The Challenges of Building and Scaling a Product

47:24 Defining Success and Financial Goals

48:19 The Desire for Financial Independence

50:38 Determining the Financial Number to Sleep Well

55:41 The Value of Personal Branding and Trust

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Why you should not talk to investors who never went through the personal pain of failing and why it most of the time comes down to the basics of running a successful business:

• Being obsessed with customers in a narrow market
• Product Market Fit is not just having a great product in a great market but also communicating it where your customers are

Timestamps:

11:00 The origin story of Notion VC, a founder/operator-led fund. An aggregator of fuckups and occasional successes

17:10 Why do we keep making the same mistakes in business?

27:00 Why anyone invests in a business. Metrics to evaluate the present, personality to see the future

33:30 Why should anyone listen to your pitch? When chaos is not avoidable with success

45:20 Are you failing because your market is too big or too small? Dangers of going too broad with your ICPs

53:50 Markets are not just what people want but where they communicate and recommend

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• Why do inexperienced, brilliant people constantly get into trouble, and how do they get out of it?
• Individual vs. team habits
• How much of our decisions is gut vs. objectivity
• Leadership porn and its connected biases

Timestamps:
6:50 How people throw words like “efficiency” and “productivity” around and do not understand them

13:25 Product operations is thinking about what can remain and what has to go in the future. 

19:50 Growing pains vs. normal pains. Why do young, smart people constantly get into really bad situations with their businesses?

25:05 Experts will always tell you that things are simple. Why tips on LinkedIn don’t work but are still popular.

30:15 How to be consistent.

38:00 The unbeautiful side of establishing habits. Individual vs. team habits

50:20 Leadership “porn”, why you should not search for broken components in organizations. Going broad first before specific.

John’s Linkedin: https://www.linkedin.com/in/johnpcutler/

Johns Blog: https://cutlefish.substack.com/

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Jasons Blog: https://world.hey.com/jason

37Signals.com: https://37signals.com/

My Blog / Newsletter: www.leahtharin.com
Linkedin: https://www.linkedin.com/in/leahtharin/
Twitter: https://twitter.com/LeahThar

#productledgrowth

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How to do a rolling planning instead of doing the depressing exercise of wasting everyone’s time for a month at the end of each year:

• Managing risks and the human component in planning
• The typical mistakes you should avoid
• What to do if you don’t agree with a company's direction

Timestamps:

04:20 Leah’s take: The operator’s perspective of yearly planning, fuzzy road mapping

07:30 Adam’s take: Conceptual thinking about planning, especially in the absence of a concrete strategy

13:20 Yearly planning and failures that are likely to happen

19:25 Resource planning and not taking care of “people”

23:15 Critical mistakes in planning

28:30 Spend some time to understand “what are your direct manager’s goals”, and overcommunicate as a manger

33:15 Calendar structure of annual planning when you own parts or the entire process

39:10 What do you do if you don’t agree with the company’s strategy?

42:50 30-60-90 day plan on how to get away from a company

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Estimations are impossible and things that are feeling impossible are possible the day after. Brian sat together with me to talk about it all including Intercom’s coming-of-age story and how they look at customer service through this new distorting lense of AI and Machine learning that is rocking our boat.

It’s a great learning piece on anything product and leadership.

Season 3 of the ProducTea: We spill the tea on how to Go to Market through Product-led Sales and Product-led Growth in B2B and the realities of senior leadership.

Timestamps:
06:30 What makes Intercom so special, and why is good customer service so difficult?
11:50 Tieing business and technology together, while AI is making quantum leaps from unuseable to “this is really good”
18:19 We are all working in a playground of opportunities that is very hard to get under predictable control
25:30 I have no idea how long this entire project might take. Days or months. No idea
31:00 Unpredictability of your output in product, you only know when you have it
36:00 Outcome-driven goals when outcomes are impossible to define?
44:00 How to build an innovative product inside a large organization by creating an artificial micro-market
52:30 We still don’t know exactly what AI displaces and it won’t. Support vs. Replacement and the resulting uncertainty.

Brians’ LinkedIn: https://www.linkedin.com/in/brian-d-2450192/
Brians' Twitter: https://twitter.com/brian_donohue