Overview of the BiggerPocketsMoney Episode
This episode compares two liquor store owners with very different outcomes: Ashley Kerr, who started a liquor store from scratch in a small rural New York town and has struggled with profitability and oversight, and Tim Delaney, who bought an existing store, stayed heavily involved for years, and grew it into a highly profitable business doing about $2.1 million in annual sales. The conversation focuses on why one store has been challenged while the other became a “cash cow,” with a strong emphasis on location, management, systems, customer data, and hands-on ownership.
The Two Businesses: Side-by-Side
Ashley Kerr: Built From Scratch, Then Became Too Hands-Off
- Opened her liquor store in November 2020
- Started in a very small rural town with roughly 3,500 people
- Store is about 1,100 square feet
- The original attraction was the idea of a liquor store as a cash-flowing, “passive” business
- In practice, she and her partner were too removed from day-to-day operations
- The store did $220,000 in sales last year
- The business required a $40,000 capital infusion in 2025 to stay afloat
Tim Delaney: Bought Existing Store, Then Learned the Business Deeply
- Bought a liquor store that was already operating but underperforming
- Was very involved for the first 5 years
- Store is about 2,200 square feet
- Serves a town of about 12,000, with several nearby suburbs adding more demand
- The store now does about $2.1 million in annual sales
- Tim still handles bookkeeping, payroll, and financial oversight, even though he only goes in about once a week
Why the Outcomes Were So Different
1. Location and Market Size Mattered a Lot
Ashley’s store is in a tiny rural market with limited traffic and few nearby businesses. Tim’s store, by contrast, benefits from:
- A larger population base
- Proximity to multiple suburbs
- More nearby competition, but also much more demand
Tim noted that liquor is often a convenience purchase, so being where people already are matters more than people expect.
2. Ashley Treated the Business as Passive Too Early
Ashley assumed the liquor store could be run like some of her real estate assets:
- Hire a manager
- Let them run it
- Collect the cash flow
That worked in her mind because she had seen a successful liquor store run that way before, but that comparison was flawed:
- That store had a better location
- It had better existing systems
- It had a strong manager
- Ashley’s store was a startup, not a mature business
3. Tim Built Systems Before Letting Go
Tim intentionally built his business to function without him:
- He trained staff slowly
- Created SOPs (standard operating procedures) in Google Docs
- Built in checks and balances
- Kept control of the money and bookkeeping
Ashley, on the other hand, had very few systems in place and didn’t know critical operational details when problems surfaced.
4. Poor Management and Weak Oversight Hurt Ashley’s Store
Ashley discovered multiple issues after finally digging into the business:
- Credit card deposit problems due to a POS/processing error
- Cash being held in the safe for up to three weeks
- Manager using the business account for personal purchases
- Manager claiming hours and responsibilities that didn’t match what employees were actually doing
- Important business accounts and online properties tied to the manager’s personal email
These issues showed how dangerous it can be to hand over a business without strong controls.
5. Tim Focused on Margins, Product Mix, and Customer Demand
Tim emphasized:
- Protecting gross margins
- Not racing to the bottom with discounting
- Building a strong bourbon program
- Selling single-barrel bourbons and even private-label bourbon
- Using customer demand data to decide what to stock
That strategy helped the store stand out and improve profitability.
Bourbon as a Growth Strategy
A major topic in the conversation was the bourbon market.
Ashley’s Bourbon Program
- Began testing rare bourbons only in the last few months
- Uses limited-release ordering windows from distributors
- Has started attracting collectors and niche customers
- Still small and developing, but promising
Tim’s Bourbon Program
- Has been a major driver of stability and margin
- Sells about 15 barrels per year
- Offers:
- Rare bourbons
- Some tequila and rye barrels
- Private-label bourbon sold only in his store
- Cultivates a loyal customer base by offering unique bottles and experiences
Key Lessons and Advice
For Ashley
Tim’s advice to Ashley was essentially:
- Get more involved with the business
- Learn the customer base directly
- Track demand systematically
- Use customer feedback to improve ordering and margins
Ashley acknowledged that she needs to:
- Spend more time with customers
- Build better tracking systems
- Reduce bottlenecks
- Stop relying on text messages for every operational task
For Tim
Tim reinforced that success came from:
- Years of hands-on work
- Gradual delegation
- Well-documented processes
- Strong financial control
He made clear that the store’s current success was not “overnight” at all—it was the result of years of setup and execution.
Operational Takeaways for Small Business Owners
What to Do
- Treat a startup business as an active job, not passive income
- Maintain ownership of all critical accounts and online profiles
- Use SOPs for repeatable tasks
- Track customer requests and buying patterns
- Control cash flow and deposits tightly
- Build systems before delegating management
What to Avoid
- Assuming a business will run itself
- Letting one employee control all information
- Using personal emails for company assets
- Delaying financial oversight until there’s a crisis
- Confusing a well-run mature business with a startup
Bottom Line
The episode’s core message is simple: a liquor store can be a strong business, but only if it’s actively managed and built with systems. Tim’s store succeeded because he was deeply involved, patient, and operationally disciplined. Ashley’s store struggled because it was treated as passive too soon, with too little oversight and weak internal controls.
The good news is that Ashley has started turning things around:
- She’s taken over more of the operations
- She’s improving inventory ordering
- She’s exploring rare bourbon as a niche
- She’s focused on profitability instead of just revenue
The conversation ends on an optimistic note: with better systems and tighter management, Ashley’s store still has room to become a much stronger business.