Jackson Speaks·September 9, 2024

Building a Portfolio of Nostalgia Restaurants | Jackson Speaks Interview

Jackson Speaks (age 27 at time of interview) and his partner Carter Andrews built a five-restaurant portfolio on Florida's 30A Scenic Highway in under 20 months, starting from zero restaurant experience. Their first acquisition was Cowgirl Kitchen in Rosemary Beach, FL — a beloved 15-year-old casual restaurant — purchased at a rich multiple with 90% seller financing on a 30-year note at 6% fixed, putting only 10% down. They improved operations by raising prices 10%, tightening cost of goods, and hiring better staff, growing EBITDA significantly. Using Cowgirl's improved financials as proof of operating competence, they cold-called the owner of Pizza By The Sea, a 4-location pizza institution also on 30A doing ~$5m in revenue and ~$1m in EBITDA, and bought it using an SBA loan plus seller carry note with roughly $300k of their own capital. Combined portfolio EBITDA grew from $1.5m at acquisition to $2.2m within 20 months. Their explicit thesis is 'nostalgic restaurants' — long-standing local brands with deep customer loyalty — which they argue are undervalued, under-competitive (few ETA buyers pursue restaurants), and provide brand equity as a buffer while new owners learn operations. They now run all five locations semi-passively with a hired director of operations and on-site managers, spending less than one day per week at the restaurants.

Deal facts

purchase price: null (undisclosed for Cowgirl Kitchen); ~$5m implied for Pizza By The Sea (5x SDE on ~$1m EBITDA)
multiple: Rich multiple for Cowgirl Kitchen (undisclosed, described as 'very rich'); ~5x SDE for Pizza By The Sea
sde ebitda: Cowgirl Kitchen: ~$500k EBITDA at acquisition, grew to part of combined $2.2m; Pizza By The Sea: ~$1m EBITDA at acquisition; combined portfolio: $1.5m total EBITDA at acquisition, $2.2m at time of interview
revenue: Cowgirl Kitchen: ~$1.5m-$2.5m; Pizza By The Sea: ~$5m across 4 locations; total ~$7m+
financing structure: Cowgirl Kitchen: 90% seller financing, 30-year amortization, 6% fixed rate, 10% equity down; Pizza By The Sea: SBA loan (First Internet Bank) + 8% seller carry note, ~$300k equity from Jackson and Carter (~6% down)
notes: Jackson Speaks and co-buyer/partner Carter Andrews purchased Cowgirl Kitchen (Rosemary Beach, FL) and then Pizza By The Sea (4 locations on 30A, FL). Combined portfolio: 5 restaurants. Both buyers were 27 at time of interview, ~25 when they bought Cowgirl Kitchen. Carter Andrews is co-equal partner. Acquisition EBITDA combined was $1.5m; grown to $2.2m in under 20 months.

Why this business

Jackson and Carter were already frequent customers of Cowgirl Kitchen and saw operational inefficiencies (old technology, no management, long wait times). Their thesis centered on 'nostalgic restaurants' — long-standing local institutions where customers have emotional ties built over years of visits. They believed the brand loyalty and embedded customer relationships created durable value and margin to hire professional management. Living at the beach was also a personal goal, and both men wanted to own businesses rather than take jobs.

What's working

Nostalgic brand equity drives repeat customers — vacationers return year after year specifically for these restaurants, providing durable revenue
Low-cost, casual positioning in a high-end, affluent tourist market creates a clear differentiation from expensive competitors
High-visibility, high-foot-traffic locations reduce marketing spend — rent functions as the marketing budget
Raised prices 10% at Cowgirl Kitchen with no customer pushback (prices hadn't been raised in 5+ years)
Implemented online ordering at Pizza By The Sea, which dramatically increased sales
Invested in new Italian stone conveyor pizza ovens capable of ~150 pizzas/hour, boosting throughput and sales
Hired a director of operations with 20-30 years of restaurant experience to manage all 5 locations
Leveraged Cowgirl Kitchen's track record and profit improvement to qualify for SBA financing on the larger Pizza By The Sea deal
Partnership structure with Carter (operations) and Jackson (finance/deals) creates complementary roles
Family/spouse alignment established early — both couples had a dinner to discuss the partnership and its implications
Reduced cost of goods by implementing purchase logs and data-driven ordering at Pizza By The Sea
Seasonality is smoothing out as 30A becomes a year-round destination, not just a summer market

What's hard

Heavy leverage — the portfolio was built almost entirely on debt (seller financing and SBA loans), and they are highly aware of this risk
SBA loan process for Pizza By The Sea was a full-time job for at least 3 months due to red tape and seller-side complications
Cowgirl Kitchen's financials were opaque at acquisition — the POS system mixed tips and sales tax, making true net sales unclear
Pizza By The Sea's POS system was even worse than Cowgirl's — no usable data at all
Labor management challenges: at Cowgirl, servers were over-scheduling themselves and undertipping customer service, requiring hiring more staff and managing turnover
Cost of goods at Cowgirl were high due to untracked, automatic ordering with no data discipline
Coaching managers without deep operational experience themselves — they were learning to coach while coaching
Summer occupancy on 30A dropped year-over-year as the area becomes a more expensive, less rental-dependent market, creating some revenue headwind
Real estate portfolio sale they planned fell through, forcing them to refinance existing properties to fund the Cowgirl acquisition instead of using the expected proceeds
High rent for prime locations is a real cost, even if it substitutes for marketing spend

Notable quotes

We weren't interested in buying these businesses to create jobs for us. I personally love deal making. I love the process of it. I love sitting down with a seller who has owned a business for 20 plus years and having them believe in us that we're going to carry on their legacy and buy it from them. That's really special to me.

The great thing about having a great brand is it gives you the margin to learn and the margin to make mistakes. Maybe their quesadilla wasn't great or maybe they didn't have the best experience with that server but they've been coming here for 10 years so you know what, we'll give them a second chance next year.

You can buy these lifetime customers and the value of them is much higher than even the multiple that you're paying for.

We had made a decent amount of profits from Cowgirl. Carter and I are both 26. We didn't want to buy a house. We don't spend a ton personally. So we really wanted to double down and invest into another business.