Lenny Rachitsky

Lenny Rachitsky
Born	Odesa, Ukraine
Alma mater	University of California, San Diego
Occupations	Writer; podcast host; angel investor
Known for	Lenny's Newsletter; Lenny's Podcast
Spouse	Michelle Rial
Website	https://lennyrachitsky.com/

Lenny Rachitsky is an American writer, podcast host, and angel investor. He is the author of Lenny's Newsletter, a paid publication about product management, growth, and careers, and the host of Lenny's Podcast, a companion interview show. Before writing full time he worked as a software engineer, co-founded the location-based question-and-answer startup Localmind, and spent seven years as a product manager at Airbnb, which acquired Localmind in 2012.

Rachitsky began the newsletter in 2019 after leaving Airbnb and introduced a paid tier the following year. Fast Company described it in 2023 as one of the five largest publications on Substack, and First Round Review later reported 1.2 million subscribers and placed it first among Substack's business titles. His site states that the newsletter has more than 1,000,000 subscribers.

Early life and education

Rachitsky was born in Odesa, in what was then the Ukrainian republic of the Soviet Union, to Jewish parents who applied to emigrate and were refused, placing them among the Soviet Jews known as refuseniks. The family obtained exit permission when Rachitsky was six and arrived in Los Angeles by way of Italy with assistance from the U.S. Jewish Federation; his mother, an economist in Ukraine, retrained as a certified public accountant, and his father, a mechanical engineer, drove taxis and limousines before returning to engineering work.

He has described himself as a shy child who read widely and taught himself to program from books bought at a local bookstore. He studied computer science at the University of California, San Diego.

Career

After university Rachitsky worked as an engineer at the web-monitoring company Webmetrics, remaining about nine years through its acquisition by NeuStar. In 2010 he left to join Year One Labs, a Montreal startup accelerator, at the invitation of its co-founder Alistair Croll, and there founded Localmind, an application that let users post questions about a specific place and receive answers in real time from people checked in there.

The Montreal Gazette reported in 2011 that Year One Labs invested up to $50,000 for roughly 20 percent equity, that Rachitsky started the company that November, that the first iPhone version launched the following March, and that the service had more than 10,000 users. Localmind drew attention at South by Southwest in 2011, and Beau Haugh joined as a co-founder that March. Reported funding totals differ: TechCrunch put the amount raised before the acquisition at $650,000, from Year One Labs, Granite Ventures, iNovia Capital, Real Ventures and others, while First Round Review reported $600,000.

Airbnb acquired Localmind in December 2012, taking on its three-person team and its technology; terms were not disclosed. Rachitsky has since characterized Localmind as a business tied to a particular moment in mobile and location technology, useful to people only rarely.

Rachitsky stayed at Airbnb for seven years, becoming one of its early product managers and leaving in 2019 as the lead of a team responsible for drawing consumers to the platform. In a conference keynote recapped by Mind the Product, he described a project to expand adoption of Airbnb's Instant Book feature by loosening eligibility rules, adding a search filter, building host tools, and running outbound campaigns; he said booking success rose from about 50 percent to more than 80 percent. He left the company after taking a three-month sabbatical.

Lenny's Newsletter

Rachitsky began writing on Medium in 2019, starting with a post about what seven years at Airbnb had taught him about building a business; it reached Medium's front page and was circulated internally by Airbnb co-founder Brian Chesky. He published seven Medium posts between April 2019 and February 2020 before moving to Substack on the recommendation of the investor Andrew Chen. Rachitsky has said the newsletter's name was Substack's default suggestion at signup and that he later tried unsuccessfully to change it. He has attributed his first roughly one thousand subscribers to two guest posts, one on First Round Review and one on Chen's blog.

The paid tier launched on April 7, 2020, priced at $15 a month or $150 a year. Paying subscribers receive a post each week and access to a private Slack community; non-paying subscribers receive roughly one issue a month. Rachitsky has said that six weeks after the launch he had about 13,000 free subscribers, about 450 paying subscribers, and roughly $56,000 in annual recurring revenue, and that free signups increased once he began charging.

Reported subscriber counts have risen over time: about 325,000 in March 2023, approaching 500,000 in August 2023, and 574,000 in January 2024. Published revenue figures conflict. CNBC reported in January 2024 that the newsletter brought in more than $500,000 a year and that the newsletter and podcast together exceeded $1 million. A 2023 analysis by Chenell Basilio for Growth in Reverse, republished in December 2024 with a note that its figures were dated, reported more than 377,000 free and more than 18,000 paying subscribers, a conversion rate of 4 to 5 percent, and estimated annual revenue from paid subscriptions above $2 million. Rachitsky has declined to disclose what share of subscribers pay.

According to Rachitsky, a typical post takes a median of about 10 hours and occasionally more than 100, and he rereads a draft dozens of times before publishing. He works with a copyeditor and a designer, and guest posts by outside contributors go through a months-long editing process. He has said that Substack's recommendation feature drives 78 percent of his free subscribers and 12 percent of new paid subscribers against a 10 percent platform fee, which is why he has stayed on the platform. Substack co-founder Hamish McKenzie has described him as the clearest demonstration of what the company's subscription model can support. By 2026 Rachitsky had reduced publication frequency from four issues a month to between two and four. Inc. has published columns by Rachitsky drawn from the newsletter.

Lenny's Podcast

Rachitsky launched Lenny's Podcast in June 2022, three years after the newsletter, after Harry Stebbings suggested the idea during a 20VC recording in March of that year. He spent several months reading about interviewing, assembling equipment, and pre-recording about ten episodes; his first guests were Julie Zhuo and Shreyas Doshi. The show settled at two roughly hour-long episodes a week, a cadence Rachitsky adopted to improve platform rankings. He told CNBC in 2024 that he spent four to five hours a week on it with help from a producer and that it brought in more than $500,000 a year.

First Round Review reported that the podcast has more than 500,000 YouTube subscribers and that episodes draw 100,000 to 200,000 downloads. Guest preparation takes two hours in most cases and five to ten when there is extensive material to review; Rachitsky sends prospective guests a standard set of questions in advance and uses AI tools to surface topics rather than to write questions. Jordan Bornstein, whose studio Pen Name produces the show, said Rachitsky declines about 98 percent of inbound guest requests on the grounds that they would not be useful to a product-focused audience. Statements made by guests are regularly reported by the business press, including Business Insider coverage of Anthropic's Boris Cherny on team structure and of Anthropic product lead Dianne Penn on using AI in management.

Community and other ventures

About three months after launching the paid tier, Rachitsky opened a private Slack community for subscribers, which First Round Review reported had grown to roughly 40,000 people. Membership benefits reported by Growth in Reverse include a weekly digest of community discussions, curated directories of product coaches and recruiters, and software discounts. He also runs a job board for product roles.

Rachitsky taught a product management course on Maven in 2021, ran it twice, and discontinued it. In 2024 he held the Lenny and Friends Summit, a 1,200-person event for product leaders in San Francisco. In 2025 he added Lenny's Product Pass, which bundles a year of access to more than twenty software tools with an annual subscription, and expanded into a small podcast network with How I AI, hosted by Claire Vo, and The Skip. He has said he keeps no full-time employees and works with about ten contractors.

Angel investing

Rachitsky began angel investing several years before leaving Airbnb, initially in companies started by former colleagues, and has said he aims to allocate about 10 percent of his net worth to it. Reported investments in 2026 include participation in a $4.5 million seed round for Pilot Protocol, an agent networking platform led by Version One Ventures, and a $12 million round for Uniti, a New York company building agentic AI tools for property managers.

Personal life

Rachitsky lives in Marin County, California, with his wife Michelle Rial, an artist and writer, and their son. He has said he schedules no meetings before 3 p.m. and declines the large majority of the roughly 200 requests he receives each week.