Why You Need to Forget Your "Mistakes" and Focus on Your Next Thing

Gary Vaynerchuk introduces a renewed focus on original podcast content and says this episode reflects his belief that “analog” business opportunities are returning: old-school, non-digital activity empowered by digital tools and AI. He introduces Ryan Chen, the 34-year-old founder and CEO of CRWD, pronounced “crowd,” a platform being built in stealth for several years. Chen explains that brands, CEOs, or CMOs request a specific group of people or business outcome, and CRWD identifies and activates ordinary people to show up at restaurants, stores, concerts, or other real-world locations and complete paid gigs.

Chen says he always wanted to be an entrepreneur and spent years building mobile apps and working in music. Both pursuits taught him that success requires large groups of ordinary people: apps need users, while musicians need fans and listeners. Existing influencer platforms and agencies could not provide the continuous, flexible supply of people he needed; agencies typically represented a finite group of 30, 50, or 100 creators. CRWD therefore evolved from a micro-influencer platform into something further downstream: a marketplace that can activate people with few or no followers.

Vaynerchuk describes CRWD as “super long-tail micro-influencer” marketing combined with TaskRabbit-like work. Chen argues that an ordinary person has commercial value because they shop at grocery and retail stores, eat at restaurants, drive, and interact with hundreds of businesses even without an audience. Vaynerchuk clarifies that this is not merely advertising to those people; businesses pay them to perform actions. A participant can sign up at joincrwd.com, form a small group with friends, browse available gigs, receive instructions and sometimes money upfront, complete the task, upload a receipt or other proof, and receive payment.

Chen gives a campaign for Kalshi as an example of technology-enabled guerrilla marketing. The company paid people the night before a Lower East Side grocery-store launch to post flyers around New York offering a $50 grocery giveaway; 4,500 people reportedly lined up the next morning, and the flyers appeared in national news coverage. For restaurants, Chen says CRWD can target people who already like sushi or another cuisine and send them to a new venue. Their first visits can generate reviews and repeat customers, solving the restaurant’s cold-start problem if the food is good.

Chen says CRWD is working with Juni, the drink associated with Kim Perel and Jay Shetty, to get thousands of people to try the product at Target. Vaynerchuk challenges the model: a person inspired by a trusted recommendation might be a better customer than someone paid to buy something. Chen answers that CRWD can run both paid trials and free-product campaigns, with the long-term goal of matching people to products and experiences they already enjoy. Vaynerchuk compares the model to sampling: even if most Costco visitors who taste a sausage never buy it, the percentage that does can justify the campaign.

For someone seeking an extra $50 or $90 a week, Chen says the participant signs up as a crowd member, may invite five to ten friends, and then chooses tasks from the marketplace. A gig might involve buying a product at Target, submitting the receipt, or attending an event. Chen identifies roughly $15 to $30 as a useful compensation range, depending on the time and effort required. Vaynerchuk imagines a participant receiving a late-night notification offering $30 to show up two miles away within an hour, and says students, active older adults, parents, and other groups may value different kinds of assignments.

Chen says CRWD initially attracted hundreds of thousands of people, but larger clients now want precise groups rather than random crowds—for example, Gen Z women at specific universities in particular cities. The company uses an AI receipt auditor and matches order numbers against backend records to catch fake receipts, attempted returns, and other abuse. Chen calls the hardest operational problem safely acquiring and deploying hundreds or thousands of people. CRWD has 15 employees, and he says he has sometimes wanted to quit during the two-to-four-year build because of the many operational hurdles, though breaking problems into individual tasks makes them solvable.

A dating app used CRWD to build a Los Angeles database of about 5,000 single men and women, then paid participants $50 to download the app, complete a survey, and hold conversations with ten interesting people. Vaynerchuk calls this “app arbitrage,” while Chen notes that participants might genuinely meet someone even though they were paid for the initial activity. They address the objection that financial incentives make marketing inauthentic: Vaynerchuk says that concern applies to some participants, but a sufficiently large targeted percentage can still produce the desired business result. Chen adds that targeting matters—sending married people to a dating app would be ineffective.

Chen recalls a Canadian artist whose label booked a nationwide U.S. tour after COVID despite weak American awareness and unsold tickets. CRWD filled venues by paying crowds to attend, sometimes including a free drink. They also discuss an iHeartMedia test in which people visited Tesla dealerships and recorded how difficult it was to find the SiriusXM button, generating hundreds of dashboard videos and consumer insights. Vaynerchuk imagines paying people $30 to walk through his Wine Library for five minutes with a camera to reveal natural shopping paths. Chen says a TrueFru campaign will send Walmart shoppers who normally skip frozen food to that aisle, potentially increasing average carts from $71 to $83.

Chen says he hired too quickly and fired too slowly, and that managing a team while everyone becomes overloaded has been difficult. He is raising capital because major clients such as Walmart need CRWD to build reliable processes rather than hear that the startup lacks funds. Asked what holds people back from going all in, Chen says he never struggled to pursue absurdly large visions, though he may not have taken the smartest routes. His years in music and mobile apps—including managing an Indian development team from midnight to 5 a.m.—gave him the audience, operational, and team-management experience that made CRWD possible. Vaynerchuk’s conclusion is to stop dwelling on apparent shortcomings and focus on the next thing.