Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own...
How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work)
Jonathan Lowenhar is the co-founder of Enjoy The Work, an executive coaching firm that helps founders become great CEOs. Over the past decade, Enjoy The Work has supported over 165 founders on their journey to becoming better leaders. In our conversation, we discuss:• The difference between being a founder and being a CEO• Common failure modes for startup CEOs and how to avoid them• The four key elements of an effective go-to-market strategy• A framework for evaluating potential acquisitions: the magic box paradigm• How to find and hire the best people• How to build a repeatable GTM machine• Why founders need to trust their intuition• Much more—Brought to you by:• Pendo—The only all-in-one product experience platform for any type of application• OneSchema—Import CSV data 10x faster• Vanta—Automate compliance. Simplify security—Find the transcript at: https://www.lennysnewsletter.com/p/how-a-great-founder-becomes-a-great-ceo-jonathan-lowenhar—Where to find Jonathan Lowenhar:• X: https://x.com/jlowenhar• LinkedIn: https://www.linkedin.com/in/jlowenhar/• Enjoy the Work: https://etw.live/lenny—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Jonathan’s background(02:56) Understanding the rhythm of well-run companies(09:20) The founder mode vs. manager mode debate(12:05) Common company failure modes(13:36) Common CEO failure modes(25:25) The magic box paradigm for selling your startup(43:07) Advice for founders on building relationships(49:28) Hiring and building an amazing team(57:11) Types of executives: architect, optimizer, scaler(59:45) Working backward in hiring(01:02:54) Four key components of a go-to-market strategy(01:15:01) Trusting founder intuition(01:19:12) Founder vs. CEO: different roles, different skills(01:20:52) Closing thoughts and lightning round—Referenced:• Founder mode memes: https://techcrunch.com/2024/09/04/those-founder-mode-memes-keep-coming/• Founder mode: https://paulgraham.com/foundermode.html• “Founder Mode” Is a Dangerous Red Herring: https://enjoythework.com/founder-mode-is-a-dangerous-red-herring/• Magic Box Paradigm: A Framework for Startup Acquisitions: https://www.amazon.com/Magic-Box-Paradigm-Framework-Acquisitions/dp/0692778047• Facebook Buys Instagram for $1 Billion: https://archive.nytimes.com/dealbook.nytimes.com/2012/04/09/facebook-buys-instagram-for-1-billion/• Chris Voss on X: https://x.com/fbinegotiator• Who: https://www.amazon.com/Who-Geoff-Smart/dp/0345504194• Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/• Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/• Nathan Blecharczyk on LinkedIn: https://www.linkedin.com/in/blecharczyk/• 4 questions Shreyas Doshi wishes he’d asked himself sooner | Former PM leader at Stripe, Twitter, Google: https://www.lennysnewsletter.com/p/shreyas-doshi-live• Traction: How Any Startup Can Achieve Explosive Customer Growth: https://www.amazon.com/Traction-Startup-Achieve-Explosive-Customer/dp/1591848369• Adam Grant on LinkedIn: https://www.linkedin.com/in/adammgrant/• This will make you a better decision maker | Annie Duke (author of “Thinking in Bets” and “Quit,” former pro poker player): https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke• How to identify your ideal customer profile (ICP): https://www.lennysnewsletter.com/p/how-to-identify-your-ideal-customer• How to get your marketing team to drive more impact: https://www.lennysnewsletter.com/p/how-to-get-your-marketing-team-to• The Five Dysfunctions of a Team: A Leadership Fable: https://www.amazon.com/Five-Dysfunctions-Team-Leadership-Fable/dp/0787960756• The Untethered Soul: The Journey Beyond Yourself: https://www.amazon.com/Untethered-Soul-Journey-Beyond-Yourself/dp/1572245379• Will & Harper on Netflix: https://www.netflix.com/title/81760197• Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o• Aura frames: https://auraframes.com/• Augie studio: https://augie.studio/• Harrah’s Entertainment: https://en.wikipedia.org/wiki/Harrah%27s_Entertainment—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
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1:34:36
Identify your bullseye customer in one day | Michael Margolis (UX Research Partner at Google Ventures)
Michael Margolis has been a UX research partner at Google Ventures (GV) for nearly 15 years. He has developed a unique approach to helping startups identify their “bullseye customer”—the specific subset of their target market who initially is most likely to adopt their product. Michael has conducted over 300 hands-on research sprints with GV portfolio companies across various industries and helped develop the “design sprint” process made famous by the book Sprint. In our conversation, we discuss:• The step-by-step process of running a bullseye customer sprint• The most common mistakes founders make when picking their first customers• Practical tips for conducting effective customer interviews• How to create simple but effective prototypes for user research• The power of “watch parties” in aligning teams around customer insights• How to apply these methods beyond typical tech startups—Brought to you by:• Eppo—Run reliable, impactful experiments• Paragon—Ship every SaaS integration your customers want• Enterpret—Transform customer feedback into product growth—Find the transcript at: https://www.lennysnewsletter.com/p/finding-your-bullseye-customer-michael-margolis—Where to find Michael Margolis:• X: https://x.com/mmargolis• LinkedIn: https://www.linkedin.com/in/mmargolis/• Website: https://www.learnmorefaster.com/• Medium: https://medium.com/@mmargolis—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Michael’s background(09:11) Bullseye customers vs. ideal customer profiles (ICPs)(12:32) An overview of the bullseye customer sprint(20:56) When to use the bullseye customer sprint(22:19) Step one: Agree on goals and key questions(23:48) Step two: Define your bullseye customer(25:52) The importance of a narrow target audience(29:00) An example of step two in action(38:24) Narrowing attributes and exclusion criteria(43:28) Step three: Recruiting and compensating participants(56:11) Step four: Creating effective prototypes(01:01:10) Step five: Drafting your interview guide(01:08:49) Step six: The watch party method(01:19:40) Common pitfalls and final thoughts(01:24:43) Closing thoughts and where to find Michael—Referenced:• Learn More Faster: How to Find Your Bullseye Customer and Their Perfect Product: https://www.learnmorefaster.com• Alcoa: https://www.alcoa.com• Dupont: https://www.dupont.com• Ericsson: https://www.ericsson.com• Google Ventures: https://www.gv.com/• Kate Aronowitz on LinkedIn: https://www.linkedin.com/in/katearonowitz/• Vanessa Cho on LinkedIn: https://www.linkedin.com/in/veecho/• How to kickstart and scale a consumer business—Step 2: Identify your super-specific who: https://www.lennysnewsletter.com/p/consumer-business-super-specific-who• When enough is enough | Andy Johns (ex-FB, Twitter, Quora): https://www.lennysnewsletter.com/p/when-enough-is-enough-andy-johns• Zipline for health care: https://www.flyzipline.com/solutions/healthcare• Jobs to Be Done framework: https://www.christenseninstitute.org/theory/jobs-to-be-done• User Interviews: https://www.userinterviews.com/• Respondent: https://www.respondent.io/• Flatiron Health: https://flatiron.com/• How to identify your ideal customer profile (ICP): https://www.lennysnewsletter.com/p/how-to-identify-your-ideal-customer• Gong: https://www.gong.io• Linear: https://linear.app• Gusto: https://gusto.com/• Humble Inquiry: The Gentle Art of Asking Instead of Telling: https://bookshop.org/p/books/humble-inquiry-second-edition-the-gentle-art-of-asking-instead-of-telling-edgar-h-schein/14739375• Figma: https://www.figma.com—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
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1:29:39
The ultimate guide to founder-led sales | Jen Abel (co-founder of JJELLYFISH)
Jen Abel is the co-founder of JJELLYFISH, where she and her team have worked with over 300 early-stage founders to learn how to sell, do early customer discovery, and set up a repeatable sales motion on the way to their first $1M ARR. In our conversation, Jen shares:• Why founder-led sales is so crucial early on• The sales process, step by step• How to craft effective outreach messages• Where to find leads• What three channels work best for outreach• What to say on your first call• How to maintain momentum• Strategies for navigating procurement and closing deals• Common pitfalls in the sales process and how to avoid them—Brought to you by:• Brave Search—A smarter way to search• Vanta—Automate compliance. Simplify security• Paragon—Ship every SaaS integration your customers want—Find the transcript at: https://www.lennysnewsletter.com/p/master-founder-led-sales-jen-abel—Where to find Jen Abel:• X: https://x.com/jjen_abel• LinkedIn: https://www.linkedin.com/in/earlystagesale—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Jen’s background(02:20) The importance of founder-led sales(08:24) The steps of a sales cycle(12:01) Tactics for effective cold outreach(16:47) Conversion rate vs. win rate(20:20) The time it takes to find product-market fit(23:06) Identifying and engaging prospects(30:58) Nailing the first phone call(34:14) Buying vs. selling(38:08) Testing the questions to ask(41:57) Avoiding common sales questions and securing the second call(43:08) Co-authoring with customers(45:06) Time-boxing service contracts(49:20) Why you should avoid demos on the first call(51:05) Dealing with procurement(54:22) The power of enterprise sales(58:14) Getting a signature(01:00:15) Choosing a focus and overcoming sales challenges(01:02:19) General timelines(01:04:27) Final thoughts and advice(01:13:32) Working with Jen—Referenced:• Wiz: https://www.wiz.io/• JJELLYFISH: https://www.jjellyfish.com/• Clay: https://www.clay.com/• A guide for finding product-market fit in B2B: https://www.lennysnewsletter.com/p/finding-product-market-fit• Airtable: https://www.airtable.com/• Figma: https://www.figma.com/• GitHub: https://github.com/• Vanta: https://www.vanta.com/• Christine Cacioppo on LinkedIn: https://www.linkedin.com/in/ccacioppo/• Glengarry Glen Ross: https://www.imdb.com/title/tt0104348/• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting• Sales Pitch: How to Craft a Story to Stand Out and Win: https://www.amazon.com/Sales-Pitch-Craft-Story-Stand-ebook/dp/B0CHY6BNDN• Sprig: https://sprig.com/• Zip: https://zip.co/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
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1:16:05
Behind the product: Replit | Amjad Masad (co-founder and CEO)
Amjad Masad is the co-founder and CEO of Replit, a browser-based coding environment that allows anyone to write and deploy code. Replit has 34 million users globally and is one of the fastest-growing developer communities in the world. Prior to Replit, Amjad worked at Facebook, where he led the JavaScript infrastructure team and contributed to popular open-source developer tools. Additionally, he played a key role as a founding engineer at the online coding school Codecademy. In our conversation, Amjad shares:• A live demo of Replit in action• How Replit’s AI agent can build full-stack web applications from a simple text prompt• The implications of AI-powered development for product managers, designers, and engineers• How this might reshape companies and careers• Why being “generative” will become an increasingly valuable skill• “Amjad’s law” and how learning to debug AI-generated code is becoming ever more valuable• Much more—Brought to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Persona—A global leader in digital identity verification• LinkedIn Ads—Reach professionals and drive results for your business—Find the transcript at: https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad—Where to find Amjad Masad:• X: https://x.com/amasad• LinkedIn: https://www.linkedin.com/in/amjadmasad/• Website: https://amasad.me/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Amjad Masad and Replit(02:41) The vision and challenges of Replit(06:50) Replit’s growth and user stories(10:49) Demo of Replit’s capabilities(16:51) Building and iterating with Replit(25:04) Real-world applications and use cases(30:13) The technology stack(33:48) The evolution of Replit and its capabilities(39:36) The future of AI in software development(44:04) Skills for the future: generative thinking and coding(47:26) Amjad’s law(50:36) Replit’s new developments and future plans—Referenced:• Replit: https://replit.com/• Cursor: https://www.cursor.com• Aman Mathur on LinkedIn: https://www.linkedin.com/in/aman-mathur/• Node: https://nodejs.org/en• Claude: https://claude.ai/• Salesforce: https://www.salesforce.com/• Wasm: https://webassembly.org/• Figma: https://www.figma.com/• Codecademy: https://www.codecademy.com/• Hacker News: https://news.ycombinator.com/news• Paul Graham’s website: https://www.paulgraham.com/• Jevons paradox: https://en.wikipedia.org/wiki/Jevons_paradox• Anthropic: https://www.anthropic.com/• Open AI: https://openai.com/• Amjad’s tweet about “society of models”: https://x.com/amasad/status/1568941103709290496• About HCI: https://www.designdisciplin.com/p/hci-profession• Taylor Swift’s website: https://www.taylorswift.com/• Andrew Wilkinson on LinkedIn: https://www.linkedin.com/in/awilkinson/• Haya Odeh on LinkedIn: https://www.linkedin.com/in/haya-odeh-b0725928/• Amjad’s law: https://x.com/snowmaker/status/1847377464705896544• Ray Kurzweil’s website: https://www.thekurzweillibrary.com/• God of the gaps: https://en.wikipedia.org/wiki/God_of_the_gaps—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
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1:04:08
Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy)
Raaz Herzberg is the chief marketing officer and VP of product strategy at Wiz. Wiz hit $100 million ARR within 18 months (the fastest growth in startup history) and, five years in, is generating over $500 million ARR. It also serves over 45% of the Fortune 100. Raaz was one of the first five employees at Wiz, joining as the first product manager, and helped the team pivot to what may be the most intense PMF in history. Before Wiz, Raaz led security products at Microsoft, including Azure Sentinel. In our conversation, we discuss:• How Wiz pivoted from their initial idea and found deep product-market fit• What Raaz learned about listening to customers• Why she moved from product to marketing, despite no prior experience• How she thinks differently as a marketer with a product background• Lessons learned from scaling a hypergrowth startup like Wiz• Much more—Brought to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Rippling—Automate HR, IT, and finance so you can scale faster• Cloudinary—The foundational technology for all images and video on the internet—Find the transcript at: https://www.lennysnewsletter.com/p/building-wiz-raaz-herzberg—Where to find Raaz Herzberg:• X: https://x.com/raazherzberg• LinkedIn: https://www.linkedin.com/in/raazh—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Raaz’s background(02:54) Early challenges and Wiz’s essential pivot(06:41) Finding product-market fit(11:31) Lessons from early customer interactions(14:54) The power in speaking up when you don’t understand something(17:46) How Wiz pivoted from their initial idea(23:52) Marketing and leadership insights(34:12) The challenges of being a marketing leader(28:05) Following the “heat” in your organization(30:22) How Raaz found success as CMO(34:01) Common CMO mistakes(36:23) Creating noise and standing out(40:28) Embracing failure and taking risks(44:53) The importance of clear communication(48:32) The “dummy” explanation(51:00) Building trust and company culture(53:45) Contrarian corner(56:34) Lightning round—Referenced:• Wiz: https://www.wiz.io/• An inside look at Deel’s unprecedented growth | Meltem Kuran Berkowitz (Head of Growth): https://www.lennysnewsletter.com/p/an-inside-look-at-deels-unprecedented• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp• Assaf Rappaport on LinkedIn: https://www.linkedin.com/in/assafrappaport/• How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen• Shardul Shah on LinkedIn: https://www.linkedin.com/in/shardul-shah-3589062/• Doug Leone on LinkedIn: https://www.linkedin.com/in/douglas-leone-a2714/• Jeff Horing on LinkedIn: https://www.linkedin.com/in/jeffhoring2009/• RSA Conference: https://www.rsaconference.com/• Microsoft acquires Adallom to advance identity and security in the cloud: https://blogs.microsoft.com/blog/2015/09/08/microsoft-acquires-adallom-to-advance-identity-and-security-in-the-cloud/• Imposter syndrome: https://www.psychologytoday.com/us/basics/imposter-syndrome• Careers at Wiz: https://www.wiz.io/careers• Setting the Table: The Transforming Power of Hospitality in Business: https://www.amazon.com/Setting-Table-Transforming-Hospitality-Business/dp/0060742763• No Rules Rules: Netflix and the Culture of Reinvention: https://www.amazon.com/No-Rules-Netflix-Culture-Reinvention/dp/1984877860/• Gong: https://www.gong.io/• The Wire on HBO: https://www.hbo.com/the-wire• Raaz’s pen holder recommendation: https://www.paper-republic.com/products/le-loop-penholder—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product. www.lennysnewsletter.com
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