In his previous appearance on the podcast, in November 2022, Jai Dolwani was the CMO of a wine subscription company that would shortly declare bankruptcy. It was his third struggling startup, he says, prompting “serious self-reflection.”
He pivoted to entrepreneurship and launched The Starters, a marketplace for fractional ecommerce talent, in late 2023. The company has thrived, having attracted more than 600 freelancers and 500 client brands.
In our recent conversation, Jai addressed the demand for ecommerce talent, tips for hiring freelancers, and plans for 2026 and beyond.
Our entire audio is embedded below. The transcript is edited for length and clarity.
Eric Bandholz: Tell us what you do.
Jai Dolwani: I’m the founder of The Starters, a company that helps ecommerce brands access top-tier fractional talent through a curated, vetted marketplace. We connect brands with experienced marketers, creatives, and technologists — professionals who’ve helped build some of the world’s best companies — so they can hire flexibly and efficiently.
Before that, I was CMO at Winc, a wine subscription company. We had recently gone public, but behind the scenes, the business struggled. A few weeks after my last conversation with you, Winc declared bankruptcy and was later acquired. I was offered a role, but it marked my third startup in a row to fail financially, prompting some serious self-reflection.
I questioned whether it was bad luck or my own shortcomings. Ultimately, I decided I needed full ownership of outcomes and became an entrepreneur. I bootstrapped the business with a $5,000 personal investment, and it’s grown steadily since. My mission now is twofold: help freelancers find meaningful, flexible work and help ecommerce brands build lean, efficient, and profitable organizations.
Bandholz: You’re building a two-sided marketplace. How did you attract talent early and create traction?
Dolwani: From day one, my philosophy was to attract the best talent first, and brands will follow. Brands are always on the hunt for top talent. To do that, we built what I believe is the most talent-friendly marketplace in the industry.
We don’t charge freelancers a commission. Unlike platforms such as Upwork or Fiverr, 100% of what freelancers bill goes directly to them. We offer private profiles. Many top performers already have jobs and don’t want a public marketplace profile visible to employers, so access is limited to vetted brands. We also avoid the race to the bottom. Most marketplaces become transactional and price-driven, with median rates of $10 to $15 per hour. We stay highly curated and vetted, focusing on strategic fit over cost.
As a result, talent on our platform competes on expertise, not price. The median rate is about $90 per hour, reflecting quality and outcomes. We’ve attracted executives from nine-figure companies and world-class specialists who would never join typical freelance platforms.
Early on, it was hard — sourcing and onboarding the first freelancers myself. Over time, strong experiences generated word-of-mouth from freelancers and brands.
Bandholz: If talent keeps 100%, how does your business make money?
Dolwani: We monetize exclusively on the brand side. Brands pay $295 per month to access the platform and hire talent through us. We charge the fee upfront, before they can view or contact freelancers, which ensures high intent. If a brand isn’t satisfied or we can’t meet its needs, we refund the fee.
This model is simple and fair. We’re not trying to build a billion-dollar, venture-backed company. We’re bootstrapped, and the pricing reflects the value we provide while allowing freelancers to keep 100% of their rates.
Payments to freelancers go through Stripe. We never touch that money — funds move directly from the brand to the freelancer. We orchestrate the experience and facilitate the connection, while the working relationship remains direct.
Most of our clients are ecommerce brands earning $1–10 million that need support but aren’t ready for full-time hires, though we also help pre-launch and nine-figure companies.
Bandholz: How do brands work with talent on your platform, and what types of expertise can they access?
Dolwani: Engagements are flexible and depend on what the brand and freelancer agree on, but I recommend a clear progression. Start with a small, capped hourly trial — around five hours — to evaluate quality. If the work doesn’t impress you immediately, it likely won’t improve. After that, work together for one to two months on an hourly basis, with a cap, to understand the output, speed, and communication.
Once expectations are clear and things are working well, shifting to a monthly retainer makes sense. Retainers reduce time tracking and keep everyone focused on outcomes rather than hours.
We now have just over 600 vetted professionals on the platform. Our core strengths are marketing, creative, and technology — everything from media buyers and fractional CMOs to designers, creative directors, Shopify developers, and heads of data and analytics. We’ve recently expanded into operations, product development, supply chain, finance, and retail expansion for consumer package brands, with more growth planned for 2026.
We’ve succeeded at our initial goal of helping ecommerce brands access better fractional talent than they’d find elsewhere. But the world is changing. As AI reduces the need for human execution, the value shifts away from task completion toward specialized knowledge and better decision-making.
Companies will win because they have deeper human insight guiding strategy. That’s where I see us going. Beyond a freelancer marketplace, we’re building a home for ecommerce expertise.
That means making knowledge accessible through courses, guides, webinars, live Q&As, consulting calls, and ongoing advisory relationships — hiring being just one option. Long-term, we hope The Starters becomes a destination for ecommerce brands to build their “human advantage” to create differentiated strategies and win.
Bandholz: Where can people follow you? Hire some freelancers?
Dolwani: Our site is Hirethestarters.com. I’m on X and LinkedIn.
