Amanda Neville transitioned from a 15-year career as a brand consultant to launching a wine shop, facing numerous unexpected challenges along the way.

While chatting with a fellow local at a sandwich shop in D.C. in 2009, Amanda learned that her neighbor often drove to Virginia for wine due to the lack of good options nearby. As a passionate wine enthusiast, this sparked the idea of creating a distinct wine shop showcasing creative decor, smart organization, and friendly, knowledgeable staff. Coincidentally, her college friend Alan Greene had retail experience and a collection of 500 wine bottles.

Although Amanda left D.C., she and Alan opened Tipsy in Brooklyn, New York. This endeavor fulfilled her dream of building a unique business focused on community engagement. Yet, the path was not without its challenges, filled with twists and turns.

Here are Amanda's top four insights she wishes she had before embarking on this wine shop adventure.

1. Be Realistic in Your Planning: Everything Takes Longer Than Anticipated. Starting a business involves countless tasks that may take significantly longer than expected, especially if it's your first time handling them.

For example, despite my extensive experience creating content for major websites, I underestimated the time it would take to craft concise, original product descriptions for each wine, including revisions of those from distributors and winemakers.

Longer task durations also mean higher expenses. So, when drafting financial models, allow for extra time in building your customer base and anticipate lower initial sales. Be prudent in your planning and ensure you have enough funds to sustain your operations during unexpected delays.

2. Learn from Others: Don't Reinvent the Wheel. Alan and I connected with many industry peers, but we missed valuable opportunities to gather more insights.

Though we believed we understood the essentials, we underestimated the complexity of inventory management. Balancing desired assortment with required quantities, order minimums, and pricing incentives from various distributors is like solving a complex puzzle. Our basement, unfortunately, is too hot due to uninsulated heating pipes, limiting our storage options until we find a solution.

Engaging in more discussions with fellow store owners and distributors would have illuminated the critical nature of adequate storage. Learn from their experiences and challenges as you prepare to establish your business. And when you think you've gathered enough information, continue reaching out.

3. Always Have a Backup Plan. Even seemingly secure tasks on your list can unexpectedly fall through. Initially, we signed a lease for a location in south Williamsburg, but should have kept searching for alternatives.

New York law mandates that liquor store entrances must be more than 200 feet from schools or churches. Despite having legal confirmation of our space, our liquor license application was denied because a charter school had moved in within that radius. We lost around $15,000 to $20,000 in rent and planning costs before ultimately finding a new space in Clinton Hill five months later.

If you're uncertain about what needs backup plans, consult your network for their insights on potential pitfalls and how to prepare for them.

4. Be Cautious with Family and Friends. My boyfriend constructed our shelves, saving us approximately $15,000 and weeks of time. However, working with close contacts can lead to sensitive discussions.

It's challenging to raise concerns about finances or deadlines with someone you're close to, especially under pressure. While the savings were beneficial, I underestimated the stress it introduced into our relationship, dominating our conversations. Assess whether involving friends or family is truly worth it; if it's only saving a few hundred dollars, it might not be.