Lenny’s Podcast88 min
Jules Walter · Jan 5, 2023
Key learnings- Build skills one at a time, dedicating a few months to each with weekly practice tied to a concrete outcome rather than just…
- Create a forcing-function outcome when learning something new, then work backwards to the questions you need answered and seek…
- Practice interviewing with dozens of mock interviews, ideally with people skilled at interviewing, since interviewers rarely give…
Lenny’s Podcast132 min
Jason Feifer · Oct 12, 2023
Key learnings- Before pursuing press, define what you need it for, such as awareness, investor credibility, or a new customer segment, the same…
- Choose outlets whose readers can actually buy or use your product; a local business gains little from a national outlet, so…
- Study how a publication covers your category and competitors, then identify the specific writer or editor, since the…
Lenny’s Podcast155 min
Hilary Gridley · Jun 15, 2025
Key learnings- When you feel criticized, skip litigating what others think and instead take one small action that demonstrates the opposite of…
- Use behavioral activation: act first on a small, concrete step, since action tends to lift mood and break negative spirals rather…
- Speak up in meetings with valuable input; fear of saying the wrong thing is the main blocker, and building the skill to take a…
Lenny’s Podcast85 min
Matt Dixon · May 30, 2024
Key learnings- Most lost qualified deals end in 'no decision' rather than to competitors, so diagnosing indecision is a core sales skill.
- Customers fear being blamed for a bad choice (messing up) more than missing out, so pushing FOMO late in a deal often backfires.
- Before pushing, judge the buyer's level of indecision using 'pings' that surface whether the hesitation is about choice overload…
Lenny’s Podcast110 min
Christopher Lochhead · Sep 17, 2023
Key learnings- Most businesses unknowingly choose to compete for a slice of an existing category; Lochhead argues category leaders capture about…
- Focus obsessively on the customer's problem, not just your solution, as Gojo did when it reframed hand washing without water to…
- Use new language (languaging) to change how people think about a problem, so they can perceive new value and be open to a new…
Lenny’s Podcast91 min
David Placek · Jun 29, 2025
Key learnings- Expect that you won't recognize the right name immediately; Placek says clients almost always believe they will, but it rarely…
- Treat a strong brand name as a long-lasting asset, since it is used more often and for longer than design, messaging, or…
- Seek distinctiveness over descriptiveness; a descriptive name like 'Cloud Pro' blends into a crowded market, while a distinctive…
Lenny’s Podcast124 min
Emilie Gerber · Mar 21, 2024
Key learnings- Press often delivers second-order value: third-party validation for sales emails, recruiting outreach, and investor or sponsor…
- For funding announcements, keep the pitch simple: amount raised, investors, and one line on why it matters, offered as an…
- Follow up respectfully every three or four days with new information, and move on to other relevant reporters after a few…
Lenny’s Podcast98 min
Kenneth Berger · May 19, 2024
Key learnings- Treat your complaints as clues: every complaint implies a dream, so reverse it into the better future you actually want.
- Articulate your wants out loud, checking whether the dream is both inspiring and credible rather than embarrassing or unrealistic.
- Hold a high bar for yes: anything short of an enthusiastic 'hell yes' should be treated as a no and explored further.
Lenny’s Podcast122 min
Nir Eyal · Dec 29, 2023
Key learnings- Distraction is mostly driven by internal discomfort such as boredom, anxiety, or fatigue rather than external pings, so identify…
- Use the 10-minute rule: when tempted to drift, set a 10-minute timer, return to the task or ride out the urge, and treat it as…
- Replace to-do lists with a calendar: time-box traction activities (work, family, health, rest) in advance so anything outside…
Lenny’s Podcast111 min
Jen Abel · Aug 23, 2026
Key learnings- Target only the executive decision-maker or their direct report (N minus one) using a 'pincer' approach, with the founder…
- Lead outreach with the executive-level value, the alpha your product unlocks for their career and business unit, not just…
- Run the intro call as an informal one-on-one conversation: no demo, no slides, no recording, and let the buyer talk first to…
Lenny’s Podcast109 min
Jeetu Patel · Feb 26, 2026
Key learnings- Distinguish a megatrend from a hype cycle: don't fight real megatrends like AI, and avoid vanity work chasing hype.
- Before investing, ask whether you have 'permission to play' and a route to mass distribution; otherwise dollars spent on product…
- Make bold bets clear and go all in once an experiment works, rather than hedging, while aligning individual success with the…
Lenny’s Podcast112 min
Chris Hutchins · Dec 18, 2022
Key learnings- Committing to a steady weekly cadence, even for just 10 weeks, puts a podcast in roughly the top few percent of all shows ever…
- Only start a podcast if you would keep doing it for free for a long time, because most shows take many months to gain traction…
- Structure a first season as a fixed number of episodes (e.g., eight) so you can test whether you actually enjoy the work before…
Lenny’s Podcast93 min
Ken Norton · Jul 24, 2022
Key learnings- Executive coaching is a partnership where the client defines success; the coach brings listening, curiosity, and challenge rather…
- Advice often delivers a short-lived boost, like cotton candy; lasting growth usually requires confronting the underlying problem…
- Leadership shifts are largely internal: reframing your operating system matters as much as learning new frameworks once you reach…
Lenny’s Podcast26 min
Interview Q Compilation · Nov 29, 2023
Key learnings- Ask 'To what do you attribute your success?' and watch for self-awareness and curiosity rather than an answer like 'luck' (Eeke…
- Ask 'What's the hardest thing you've ever done?' to learn how a candidate defines difficulty, how they overcame it, and how much…
- Use the teleportation-device 'Eigenquestion' exercise: candidates may ask only two questions, then must plan, revealing how they…
Lenny’s Podcast95 min
Donna Lichaw · Feb 25, 2024
Key learnings- Treat the stories you tell yourself as hypotheses: check them against real feedback from colleagues instead of assuming they are…
- Start leadership growth from the inside out: lead yourself first, then one-on-ones, teams, and the wider business.
- Ask how a limiting habit or belief, like imposter syndrome, currently serves you before trying to suppress it.
Lenny’s Podcast103 min
Ryan Hoover · Aug 7, 2022
Key learnings- Before launching on Product Hunt or elsewhere, define the goal first: customer acquisition, recruiting, fundraising, feedback…
- Write launch taglines and descriptions the way customers describe your product to friends, not in polished PR language, since…
- Use the product gallery as a visual story, such as a before-and-after or an evolution, since visitors look at visuals first on…
Lenny’s Podcast78 min
Keith Yandell · Feb 9, 2023
Key learnings- Hire people better than yourself, then get out of the way; the most valuable managers slowly step back as their team members…
- Write a 'How to work with me' document that states your expectations, known growth areas, and commitments to your team; it helps…
- Help people find their next job, even outside the company; it surfaces retention risks early, lets you plan backfills, and builds…
Lenny’s Podcast85 min
April Dunford · Jun 9, 2022
Key learnings- Weak positioning shows up across the funnel: confused prospects, sluggish middle-of-pipeline deals, and churn after the sale, so…
- Start positioning by identifying competitive alternatives, including the status quo, since roughly 40% of B2B deals are lost to…
- Turn a list of differentiated capabilities into customer value, then group them into two or three value themes that only you can…
Lenny’s Podcast88 min
Jonny Miller · Jan 28, 2024
Key learnings- Calm the body first: changing breath and physiological state tends to shift thoughts and feelings faster than trying to reason…
- Use a longer exhale than inhale (e.g., 4-4-8 breathing) to downshift; a longer inhale or energizing breath can raise activation…
- Build a daily practice of two to five minutes in the morning so calming techniques come naturally in stressful moments, since…
Lenny’s Podcast99 min
Jessica Hische · Oct 20, 2024
Key learnings- Startups can launch with a quick, internally made logo, then invest in a custom refresh once the company is more stable, avoiding…
- Signs it's time to upgrade a logo include a broader rollout of the brand, printing swag or hosting events, or needing assets that…
- A custom logo or typography makes your brand harder to copy than a freely available font, which matters once success attracts…
The Looking Glass podcastJun 9, 2026
Jun 9, 2026
Key learnings- Treat sales as a craft worth mastering, not a lesser discipline; understanding how customers buy makes product leaders far more…
- Learn to listen closely to what customers are actually trying to accomplish before proposing solutions or pitching value.
- Build trust through consistent follow-through, since credibility compounds over repeated interactions with buyers and internal…