Ryan Petersen

Petersen lost a bill of lading, the single sheet of paper that establishes legal title to a shipping container, and watched fines run up at roughly $1,000 a day while three parties re-executed the paperwork. Eight years passed before he did anything about it.¹

Ryan Petersen is the founder and CEO of Flexport, a company that acts as a technology-driven middleman for global freight: it books ocean and air cargo space, handles customs clearance and compliance paperwork, and gives importers and exporters software to track shipments that traditionally moved through fax machines and email chains. Petersen built the company after years as a frustrated customer of the freight industry, and has run it almost continuously since 2013, with one voluntary handoff to an outside CEO that he later reversed.

Background

Petersen grew up in Bethesda, Maryland, the son of a biochemist mother who also ran her own small business and a father who worked as a programmer, including writing software for the Department of Defense. He credits this upbringing as an informal entrepreneurial apprenticeship, tracing habits back to being paid to run his mother's office snack operation as a nine- or ten-year-old and working flea markets as a young teenager.

At around 17, alongside his brother David and a business partner, he began importing electric scooters and motorbikes from China and reselling them in the United States, eventually becoming an early US dealer for the Chinese motorcycle maker Geely. He earned a bachelor's degree in economics from Berkeley in 2002, then lived in mainland China running supply-chain operations for the import business, which exposed him directly to the inefficiencies of freight forwarding. In 2007, he co-founded ImportGenius, a shipping-manifest data company, with his brother and Michael Kanko. He later earned an MBA from Columbia Business School, graduating in 2008, financing roughly $140,000 in tuition debt through three part-time jobs: writing case studies for the business school, teaching GMAT preparation, and running an SEO consulting business.²

Getting started

The lost bill of lading dated to the motorbike-import period, and Petersen has cited the roughly eight-year gap between that incident and founding Flexport as his own case of ignoring an obviously broken problem for too long before deciding to fix it.

Petersen applied for a US freight-forwarder license in 2010 and worked on Flexport alone for four years while it was pending, funding himself through his side jobs rather than raising capital. Before the license was granted, he put up a marketing-only landing page describing the idea, and companies including Foxconn, Cargill, and Saudi Aramco signed up unsolicited, which he has pointed to as the first evidence the business would be large.¹ The license came through in March 2013; he immediately hired several developers, then went through Y Combinator and raised outside capital for the first time, pitching Flexport as "the first licensed US customs brokerage built around a modern web application," a framing he has also called "TurboTax for customs."¹

What he built

Flexport grew from that single-license operation into a full freight forwarder handling ocean, air, and trucking logistics, customs brokerage, and trade financing, eventually moving roughly 1 percent of all US containerized ocean trade. It raised more than $2 billion in venture capital, including a $935 million Series E in February 2022 led by Andreessen Horowitz that valued the company at $8 billion, its peak disclosed valuation.¹ In 2023, Shopify sold its in-house logistics operation to Flexport for a roughly 13 percent equity stake. Flexport also acquired the technology and engineering team of the trucking marketplace Convoy in November 2023, after Convoy shut down, at a price Petersen called modest relative to the value acquired; it sold that platform on to DAT Freight & Analytics in July 2025.

Petersen stepped back from day-to-day management in 2022, becoming executive chairman and bringing in Dave Clark, a former senior Amazon logistics executive, first as co-CEO and then as sole CEO by March 2023. Under that leadership Net Promoter Score fell from the mid-70s to 17 and shipment volumes stopped growing; Clark resigned in September 2023 and Petersen returned as CEO.³ Since then Flexport has emphasized tariff-refund recovery and customs auditing.⁴ It also expanded into trade financing with BlackRock, and by 2025 reported roughly $450 million in net revenue, up about 30 percent year over year, with Petersen expecting the company to come out roughly break-even and targeting about $100 million in EBITDA exiting 2025.

How he operates

Petersen's stated method centers on staying close to frontline operations rather than managing through reports. He describes a company organized around cross-functional "squads" that each serve a set of customers, a design he compares to an immune system responding directly to problems rather than a nervous system waiting on instructions from the top; he attributes the 2022 crisis partly to management drifting away from that model toward centralized, task-based efficiency.³ He conducts what he calls "gemba walks," borrowed from the Toyota Production System, and believes leaders should be able to explain their industry's complexity to a smart layperson, since obscurity is often where mediocre performance hides.² He believes founders retain a form of authority hired executives lack, since they will still be present years later to live with the consequences of their decisions, and tells employees after every large fundraise that a valuation is not a fact but a probability-weighted guess about the future.¹ His approach rebuilds an entrenched, paper-based industry from first principles with software, drawing on deep, self-taught domain knowledge of trade and shipping law.

Where things stand

As of the mid-2020s, Petersen remains CEO of Flexport, which he intends to keep growing toward an eventual public offering without a fixed timeline. He is also a partner at Founders Fund, a role he now describes as secondary to running Flexport, and has spent time lobbying in Washington on tariff enforcement and trade-fraud issues.⁴ He is married to journalist Olivia Zaleski and has two daughters.

Key facts

• Applied for Flexport's freight-forwarder license in 2010 and worked alone on the company for four years before it was granted in March 2013.
• Funded that period through side jobs: writing Columbia Business School case studies, teaching GMAT courses, and running an SEO consulting business.
• Flexport raised more than $2 billion in venture capital, including a February 2022 Series E of $935 million at an $8 billion valuation.
• Stepped back to executive chairman in 2022, watched Net Promoter Score fall to 17 under an outside CEO, then returned as CEO in September 2023 and restored NPS to the low 70s within months.
• Co-founded ImportGenius, a shipping-data company, in 2007 with his brother David and Michael Kanko before founding Flexport.
• Acquired Convoy's technology stack in November 2023 at a price he called modest relative to the value acquired, then sold the platform to DAT Freight & Analytics in July 2025.