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How to foster innovation and big thinking | Eeke de Milliano (Retool, Stripe)

Eeke de Milliano is the Head of Product at Retool and a former product lead at Stripe. In this episode, we discuss how any team can become an innovation machine. We talk about how a culture of writing led to a team of rigorous thinkers at Stripe. We cover tactics to breed innovative teams that you can replicate at your own company: From embracing retrospectives to creating systems that give individuals the "permission to think big". Eeke shares her framework for prioritizing resources between core products, strategic initiatives, and big bets, and how it helped Retool launch three new products in a year. She also gives a comprehensive overview of the right level of process for companies of different sizes, and how to build a talent portfolio. — Brought to you by Miro—A collaborative visual platform where your best work comes to life: https://miro.com/lenny | Notion—One workspace. Every team: https://www.notion.com/lennyspod | Eppo—Run reliable, impactful experiments: https://www.geteppo.com/ Find the full transcript here: https://www.lennysnewsletter.com/p/how-to-foster-innovation-and-big Where to find Eeke de Milliano: • Twitter: https://twitter.com/eekedm • LinkedIn: https://www.linkedin.com/in/eeke-de-milliano-3b05a629/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ Referenced: • Snir Kodesh on LinkedIn: https://www.linkedin.com/in/snirkodesh/ • Stripe: https://stripe.com/ • Stripe’s operating principles: https://stripe.com/jobs/culture • Retool: https://retool.com/ • Brian Krausz on LinkedIn: https://www.linkedin.com/in/bkrausz/ • Retool Workflows: https://retool.com/products/workflows/ • Retool Mobile: https://retool.com/products/mobile • Retool Database: https://retool.com/products/database • Ian Leslie on “Being Human in the Age of AI”: https://www.econtalk.org/ian-leslie-on-being-human-in-the-age-of-ai/ • Claire Hughes Johnson on LinkedIn: https://www.linkedin.com/in/claire-hughes-johnson-7058/ • Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212 • Linear: https://linear.app/ • Bird by Bird: Some Instructions on Writing and Life: https://www.amazon.com/Bird-Some-Instructions-Writing-Life/dp/0385480016/ • Lex Fridman Podcast: https://lexfridman.com/podcast/ • EconTalk: https://www.econlib.org/econtalk/ • The White Lotus on HBO: https://www.hbo.com/the-white-lotus • Gong: https://www.gong.io/product-demo/ • FullStory: https://www.fullstory.com/ • Rewind: https://www.rewind.ai/ In this episode, we cover: (00:00) Eeke’s background (03:36) Eeke’s time at Stripe (08:58) Why Stripe didn’t add PMs until hitting around 100 employees (11:03) Why being a PM is not for everyone (12:22) Stripe’s internal culture guide (17:36) Stripe’s operating principles  (20:52) Why isn’t every team innovative? (23:21) Retool’s “crazy ideas” list  (27:27) How to cultivate a failure-safe space  (28:47) Fostering risk-taking and innovation (32:03) The three products Retool launched this year (35:06) How Retool was able to launch several products at once (38:00) The amount of process needed through different stages of growth (45:37) Why you should build products for your “best users” (47:34) Build the scooter, not the axle (why you should make something simple but functional first) (48:37) The 70-20-10 framework for investing resources and time (49:57) Finding time for maintenance and bug fixes (50:59) How Retool’s PMs keep close to customers (53:29) Building product in a sales-led org vs. product-led growth  (56:10) The product talent portfolio: how to build diverse, balanced teams (58:43) Lightning round Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Eeke de MillianoguestLenny Rachitskyhost
Feb 1, 20231h 2mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Inside Stripe and Retool: Building Innovative Products Without Crushing Creativity

  1. Eeke de Milliano, Head of Product at Retool and early PM at Stripe, unpacks how Stripe’s culture, operating principles, and writing rigor fueled sustained innovation and strong product decisions.
  2. She explains how Retool has launched three major products in a year by treating them as small, funded startups, keeping teams tiny and independent until they prove real traction.
  3. A major theme is balancing process and creativity: using “minimum viable process,” escape hatches, and permission to think so top performers can stay innovative while the org scales.
  4. Eeke also shares practical frameworks for fostering big thinking, structuring product portfolios and talent portfolios, and keeping PMs deeply connected to customers in both PLG and sales-led contexts.

IDEAS WORTH REMEMBERING

5 ideas

Use writing and first-principles thinking to raise decision quality.

Stripe’s heavy writing culture and insistence on first-principles reasoning (not “best practices”) forced clearer thinking, better decisions, and a shared mental model across the org.

Distinguish one-way vs. two-way door decisions to move faster.

Borrowing from Amazon, Stripe rigorously asked whether a decision was reversible; pricing, for example, is often treated as irreversible but can be changed later, enabling faster iteration.

Normalize failure and increase at-bats to unlock innovation.

Leaders must publicly surface and celebrate learning from failures (e.g., retros shared with the org, talks at all-hands) and keep bets small and fast so the stakes of any single failure are low.

Create explicit structures that give teams “permission to think.”

Retool uses “Think Bigger” sections in planning docs and an annual “Crazy Ideas” doc—explicit prompts that ask everyone for 10–100x ideas, some of which have become shipped products.

Start new products as tiny, independent startups inside the company.

Retool launched Workflows, Mobile, and Database by staffing each with 1–2 people initially, keeping them separate from the core org, and requiring them to prove ROI before scaling headcount.

WORDS WORTH SAVING

5 quotes

Process by definition is variance reducing… while you’re reducing the standard and bringing folks up to the average, you’re also bringing other folks down to the average.

— Eeke de Milliano

Stripe was really good at making a lot of really good decisions all the time, big or small.

— Eeke de Milliano

You have to give teams permission to think.

— Eeke de Milliano

Build for your best user, not your worst user.

— Eeke de Milliano

We treated the new products like startups where Retool is the VC.

— Eeke de Milliano

Stripe’s culture, operating principles, and writing-first decision-makingWhen and why to introduce product management in dev-focused companiesHow to foster innovation, embrace failure, and create space for big thinkingLaunching and organizing around multiple new products at RetoolDesigning process by company stage and using “minimum viable process”Balancing PLG and sales-led motions and tight PM–sales collaborationBuilding a balanced “product talent portfolio” and PM skill mixes

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