Workstream CEO Desmond Lim: The first check was from Eric Yuan for $25,000, issued in June 2018
Desmond Lim, CEO of Workstream, recalled that the company's first angel check came from Zoom CEO Eric Yuan, amounting to $25,000, issued in June 2018.
The two met earlier. In June 2016, Lim had just arrived in San Francisco and interviewed Yuan as a freelance journalist. After founding Workstream, which focuses on recruiting and onboarding hourly workers, in 2018, Yuan became one of the earliest angels and handwrote the check in the San Jose office. Lim stated that Yuan has followed up with every round of investment, totaling over seven figures.
He summarized four points: first ask for advice, not money; start with friends and mentors who already believe in you; keep progress synchronized through emails or meetings; sell the founder's story and vision, not just numbers. His judgment is that the first angel often comes from the existing network.
Since then, Workstream has received funding from Founders Fund, Mark Cuban, Jay-Z, and others, raising approximately $120 million in total. In the B round, they received over ten term sheets, led by BOND and Coatue. Lim has also personally invested in over twenty startups. The company's first paying client was a Palo Alto café, where the three founders went door-to-door to sell their service.
This narrative frames the $25,000 check as an entry point for subsequent institutional rounds: establishing a two-year relationship among immigrant founders before cashing in on trust at launch.
In market mechanisms, this is about reputation capital coming first, followed by cash: small checks from publicly listed or high-growth founders reduce due diligence costs in later rounds. Beneficiaries are entrepreneurs who can convert interviews, alumni, and immigrant networks into cap tables; those under pressure are projects without updated relationships, which can only cold-start institutional seed funding. Funds enter hourly labor software from the personal account of the Zoom founder and are then amplified by growth round funds.
Public records can verify the check date, amount, and subsequent follow-on investments, but the list of the next companies he angel-invested in is not detailed in this post.
Source: Public information
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Lim first met Yuan in his capacity as a journalist, effectively turning a cold email into a productive interview, and only two years later did that same relationship yield a $25,000 check. This contrasts with the process of dedicated venture capital: there was no memo, just a shared narrative among immigrant founders. Yuan issued the check without probing product details, indicating that early pricing is based on people, not the model of hourly recruitment software. The subsequent entry of Founders Fund and Coatue treats this personal check as a credibility filter that has already been passed.
Capital moves from personal checks to growth rounds, with the path being the same investor repeatedly increasing their stake. Yuan's follow-on investment in every round locks the angel relationship into long-term shareholders. Workstream sells a recruitment funnel for hourly positions in restaurants and retail, yet the list of investors resembles a mix of consumer internet and hedge funds. The motivation is to use a celebrity cap table to lower the explanation costs for the next round; the strategy is to keep the first check in the wallet as an external narrative.
In comparison to Stripe and Airbnb, which were early funded by successful founders writing small checks, and today's founders of Vercel and Figma intensively acting as angels, the industry position remains one of network control: those who can maintain two years of updates before launching can shift seed rounds from institutional auctions to internal subscriptions.
This represents capital concentration: early equity is first allocated within the founder circle before being opened to institutions. The mechanism is to replace funding pitches with requests for advice, continuously synchronizing as an alternative to quarterly reports, with stories replacing early revenue.
ABAB News · Cognitive Laws
The first check usually comes from someone who has already met you.
Those who ask for advice are more likely to get money than those who ask for valuation first.
Once small trust is made public, later institutional rounds just need to stamp their approval.