Simon Beckerman, the Italian entrepreneur behind the second-hand clothing marketplace Depop, has reflected on his journey from financial hardship to business success, detailing the challenges and motivations that shaped his career. Now 52, Beckerman founded Depop in 2011 while struggling to sustain a small Milan-based culture magazine amid the growing dominance of digital media.
Depop, launched as a peer-to-peer platform for vintage and second-hand fashion, capitalised on the rising influence of mobile technology and the internet. Beckerman recognised early on that people were increasingly using mobile devices, inspiring him to create a marketplace that combined ecommerce with social interaction. The app’s user base grew significantly over the following decade, leading to its 2021 acquisition by Etsy for £1.1 billion. Beckerman reportedly earned £45 million from the sale, excluding subsequent stake sales.
Despite the financial rewards, Beckerman has openly discussed the intense stress and burnout experienced while scaling Depop. He stepped down as CEO within a few years and took a year-long sabbatical to recover. In late 2020, he co-founded Delli, a marketplace aimed at independent food producers. He has largely self-funded the venture and retains a roughly 40% ownership stake. Beckerman recently stepped back from day-to-day operations at Delli as he prepares to become a father for the first time.
Beckerman’s early work experience included playing as a DJ at clubs in Milan and running a graphic design studio with his brother. The family also produced a magazine called Pig (People in Groove) that focused on underground creatives and fashion. Financial struggles during this period were significant, with Beckerman describing himself as “always half broke” before Depop’s success.
When asked about his motivations, Beckerman acknowledged money as an important priority after years of hardship, particularly as he witnessed his parents’ financial difficulties. He emphasised that, while earning money was critical, teaching people how to manage and spend money effectively was equally important.
Beckerman’s initial salary at Depop was modest, but increased when the company relocated to London in 2012. He made several secondary stake sales prior to the Etsy acquisition, generating liquidity but also noting that he might have earned more had he waited for the company’s ultimate valuation.
The exit changed his relationships and mindset, he said, with some friends altering how they interacted with him. Despite the financial security, Beckerman admitted lingering anxiety around spending large sums, describing a persistent “trauma” related to money. Even years after the sale, he remains cautious about expenses such as travel upgrades.
Alongside Delli, Beckerman has diversified his investments. He has contributed to venture funds like HV Capital and Balderton and invested in several startups, including an early stake in Stripe via a friend’s SPAC fund and a substantial investment in SpaceX. Although many of his smaller startup investments have yet to be profitable, Beckerman continues to back new ventures, considering a future shift into broader investment activities.
Throughout his career, Beckerman has demonstrated resilience amid financial uncertainty and a continuous drive to build and innovate, even after achieving significant entrepreneurial success.