Founder Fireside - A chat with Jai Dolwani

If you’re a wine fan there’s a good chance you heard of Winc. 

A DTC wine platform, Winc launched in 2011 before hitting high gear during the COVID lockdowns. A 77% revenue growth spurt between 2019 and 2020 was met with VC funding and an eventual IPO in 2021. 

Jai Dolwani joined Winc during that time. A young man in his early 20’s, Jai nevertheless rapidly rose up the executive ranks, overseeing Winc’s growth and expansion. For a brief period, it seemed like a dream job. 

Until it all came crashing down. As the pandemic ended and the free money of the ZIRP era dried up, Winc’s debts mounted. They were forced to file Chapter 11 in late 2022. 

Devastated, but not defeated, Jai pivoted to a new, bootstrapped venture - The Starters. A premium freelance platform for DTC and e-commerce brands.

We recently caught up with Jai to talk about his time at Winc, how it influenced his thinking with The Starters, and what he can teach other founders. 

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Hard lessons learned

DTC Times: Can you share your experiences before launching The Starters, particularly at Winc, and how they influenced your new venture?

Jai Dolwani: “I joined Winc right as the pandemic was kicking off in early 2020 as the Director of Retention. I was tasked with figuring out how to retain the massive influx of customers we had at that time. Everyone wanted to get wine at home, and Winc was an online wine subscription.”

DTC Times: How did your role evolve during your time there?

Jai Dolwani: “As I started to solve a lot of the problems related to customer retention, I was promoted to General Manager and then to CMO to take on new challenges.

I owned a $50 million P&L, and we went public in November 2021. However, while the e-commerce business unit was profitable, the overall business fundamentals were shaky. We were trying to expand aggressively into wholesale, launch new product categories, build our own brands, and acquire other businesses - but we were losing about $10 million a year.”

DTC Times: That must have been tough, especially with the IPO happening. What challenges did you face post-IPO?

Jai Dolwani: “After we went public, the market started to crash, and our stock price dropped 95% in just three months. 

At that point, we had to go through a very aggressive layoff cycle. As someone who had just hired many of these people, it was incredibly difficult. I was 25 or 26 years old at the time and had no idea what I was doing. I had to lay off people I had considered friends, who had given up great jobs to come to our business.”

DTC Times: That’s a challenging situation for anyone. Did that experience shape your thoughts about hiring?

Jai Dolwani: “Absolutely. That experience made me think about how I could have built the team more sustainably. I started looking into the world of fractional talent after realizing that we needed to keep the wheels turning without increasing operational expenses. 

I turned to leveraging freelancers through staffing agencies, but I quickly learned that they were incredibly expensive. For instance, I was paying $150 an hour to a staffing agency, only to find out that the freelancer was making $50. There was a huge markup, and it led me to realize how hard it is to find good talent through traditional means.”

DTC Times: How did those experiences ultimately inspire you to start The Starters?

Jai Dolwani: “My work at Winc ultimately inspired me to build The Starters. I thought, ‘Can I create a business that helps other entrepreneurs build their teams in a more sustainable way so that they don’t have to learn the hard lessons that I did?’”

How The Starters helps both brands and freelancers

DTC Times: Let’s talk about The Starters. What sets it apart from other freelance hiring platforms?

Jai Dolwani: “The Starters is built on the idea of being freelancer-first, so we can attract the best talent. I fundamentally believe that intermediaries should not take a cut of freelancers' salaries. They already have 30-40% going to the government, so they don’t need us taking another 20%. Our entire belief is: how can I be as freelancer-friendly as humanly possible? This approach allows us to attract the best freelancers.”

DTC Times: That’s an interesting business model. Can you elaborate on how it works?

Jai Dolwani: “We charge brands a flat subscription fee of $295 a month. This gives them access to hire as many people as they want without the burden of ongoing rate markups or commissions. By requiring an upfront payment, we ensure that only serious brands join who are ready to hire, which saves everyone's time.”

DTC Times: How do you ensure the quality of talent on your platform?

Jai Dolwani: “Our platform only accepts a small percentage of applicants. We have a three-month waiting list for freelancers because we want the best talent. We’ve brought in top-tier professionals, including CMOs and VPs from successful companies, who would not otherwise freelance.”

DTC Times: It sounds like you have a very selective process. How does that benefit the brands that use your service?

Jai Dolwani: “The Starters isn’t just about connecting brands with freelancers; it’s about creating a curated experience. When brands sign up, they take a quick quiz to determine their needs, and I personally reach out to help them navigate the platform. 

Our aim is to provide a tailored service that ensures brands find the right fit quickly and efficiently.”

DTC Times: How did you acquire your first customers?

Jai Dolwani: “It was a real struggle at first. I remember leaving Winc, and the new owners asked me to consult for them for a bit. I told them I would do it for free, but they had to sign up for The Starters. That became my first customer. Initially, I was posting on LinkedIn and getting a couple of people to sign up here and there. If I got one new customer a week, I was delighted.”

DTC Times: And how did you bring in your first freelancers?

Jai Dolwani: “When I first launched the business, I leveraged my existing network. I had a list of successful e-commerce brands, so I hopped on LinkedIn Sales Navigator, searched for the people working behind those brands, and reached out to them directly. I probably sent about a thousand LinkedIn DMs. This initial outreach was how I got my first hundred freelancers on the platform.”

DTC Times: It sounds like a well-thought-out approach. What do you see as the main advantage of this model?

Jai Dolwani: “By focusing on quality rather than quantity—having only around 400 freelancers—we can ensure that our clients have access to top talent that meets their specific requirements. We want to prevent the common pitfalls associated with larger platforms, where the sheer volume can lead to overwhelming options and misaligned expectations.”

Lessons for founders

DTC Times: What insights can you share with other founders, particularly around hiring and staffing?

Jai Dolwani: “One of the most crucial lessons I learned is that early-stage founders should do almost everything themselves before delegating responsibilities. I always say, ‘Embrace a hands-on approach initially.’ In those early phases, it’s vital to develop a deep understanding of every aspect of the company—from customer acquisition to product development and marketing strategies.”

DTC Times: So, how do you recommend founders approach the early stages of their business?

Jai Dolwani: “Founders should focus on handling tasks with a network of advisors and consultants until they reach a significant milestone, like $1 million in revenue. At that point, they can start considering hiring. I did everything I could in the early days of The Starters, even running paid search ads myself. I hired a freelancer for a few hours to help me set things up, but I wanted to learn the ropes firsthand.”

DTC Times: That makes sense. Once they reach that milestone, what should they focus on next?

Jai Dolwani: “Once founders hit that $1 million threshold, they need to evaluate whether they truly have product-market fit. I advise them to ask critical questions: ‘Are my customer acquisition costs low enough? Are my reviews stellar? Are people repeat purchasing?’ It’s essential to ensure that they’re not rushing to scale if these fundamentals aren’t in place.”

DTC Times: And after validating those fundamentals, what comes next?

Jai Dolwani: “I highly recommend leveraging fractional talent instead of hiring full-time employees right away. This allows businesses to access high-quality expertise without the financial burden. I brought in specialists like paid social media buyers and creative strategists at The Starters, which freed me up to focus on strategic initiatives.”

DTC Times: What other factors should founders consider?

Jai Dolwani: “Creating a strong company culture is also critical from the very beginning. When I was at Winc, I learned that a positive work environment leads to better performance and employee retention. It’s vital to promote open communication and collaboration, especially during challenging times.”

DTC Times: How about when it comes to funding? What advice do you have for founders considering venture capital?

Jai Dolwani: “I’ve learned to be very thoughtful about the implications of accepting external funding. While venture capital can provide essential resources for growth, it can also lead to pressures that may not align with the founder’s vision. I wanted to ensure that my decisions at The Starters would not be unduly influenced by investor pressures, allowing me to maintain control over the company’s direction.”

DTC Times: That’s great insight. What else should founders keep in mind?

Jai Dolwani: “Continuous learning and adaptation are crucial in this fast-paced industry. I always emphasize, ‘The e-commerce landscape is ever-changing, and what works today may not work tomorrow.’ Staying informed about industry trends, customer preferences, and new technologies is vital. This not only helps founders pivot when necessary but also positions them as thought leaders in their field.”

In summary, Jai noted that Founders should embrace a hands-on approach initially, validate their business model before scaling, be cautious with funding decisions, and foster a culture of continuous learning and support. By doing so, they can build resilient businesses that not only survive but thrive in the competitive e-commerce landscape.

• You can follow Jai Dolwani on X here. 

• Be sure to check out The Starters here.

• Don’t forget to visit Elevar to find out how they can improve your data tracking and integrity before BFCM.