We Bought a “Boring” Business. Running it Was Another Story.

Buy a boring business, they said. It’ll be easy. It’ll be fun.

That’s the dream Andrea Palacio and her husband chased when they bought a landscaping company.

The road got bumpy fast, but they still added around $300,000 in equity value in just a couple of years.

Andrea Palacio runs AndreaPalacio.ai, where she helps other business owners put AI to work.

But before that, she and her husband lived on a sailboat for 4 years while running an e-commerce business selling pet supplies on Amazon and Shopify.

When that business stalled, they sold it and went looking for something new. They landed on a South Florida landscaping company, thinking it would be steady and mostly hands-off. Instead, almost everything went wrong at once.

Tune in to Episode 750 of the Side Hustle Show to learn:

how Andrea rebuilt after losing most of her team and clients
how simple AI tools gave her back 20+ hours a month
what buying a business taught her about leadership

Why a Landscaping Business?

After 4 years on a sailboat, Andrea and her husband felt their e-commerce growth stall.

To keep competing with big pet-supply sellers, they would have needed to invest hundreds of thousands of dollars. They didn’t want that risk, so they sold and looked for a new path.

Andrea watched a lot of YouTube videos about buying businesses. The pitch was simple: buy a company that already works, put a manager in place, and step back.

They wanted something that fit both of them. Andrea is strong online with marketing and customers. Her husband is very hands-on.

Landscaping felt recession-proof, since in Florida everyone has to keep their lawn cut, so they went for it.

The Deal That Fell Apart

They bought the company for $470,000, paying about a 2.3x multiple on net income.

To fund it, they used an SBA loan and put their personal assets, including their home, up as collateral. Quitting was never an option.

Then things unraveled. The seller was supposed to train them, but he disappeared just 5 days after the sale.

Soon after, the manager quit and told the crew they were better off finding other jobs. The team dropped from 12 employees down to about 2.

A Brutal First Month

At the time, Andrea had a 7-month-old and was pregnant with her second son.

She was fielding 50 calls a day while handling marketing, admin, and customer service.

Revenue fell from $70,000 a month to $40,000 a month, and her husband had to do the labor himself.

Digging Out of the Hole

The first move was running Google Ads to win back clients. It was expensive to learn, and they wasted money before getting it right.

Finding workers was even harder. Andrea says she might interview 100 people, have 5 show up, and find just 1 who was decent.

Taking over an existing business and then improving it is its own skill.

Jono Santamaria took the same approach with a laundromat, making a series of changes to grow revenue once he owned it.

Learning to Sell

About half their revenue was recurring lawn care.

The other half came from bigger custom and enhancement jobs, which they didn’t know how to sell. They lost their large commercial clients, like shopping plazas paying $2,000 to $3,000 a month.

Andrea’s husband learned sales the “fake it till you make it” way.

Over about a year, they rebuilt revenue to $60,000 to $65,000 a month, sometimes hitting $70,000, while working 80-hour weeks.

Using AI to Get Time Back

The 80-hour weeks left Andrea feeling like she couldn’t be present for her kids. Something had to change.

Her sister mentioned that ChatGPT had just come out.

Andrea, who calls herself tech-curious, started playing with it and imagined AI handling her phone calls and chasing late payments.

Trial and Error

She first hired an Upwork freelancer to build her idea. Five months later, she had nothing.

A second freelancer built an automation on Make that sent clients a photo, pulled from their CRM, after every service, plus a follow-up text.

Happy clients were sent to a Google review; unhappy ones went to a complaint form.

They also switched from paper scheduling to a CRM called Jobber.

Then Andrea taught herself Make on YouTube and built the AI receptionist she first imagined, which booked appointments right inside Jobber.

She notes tools like Claude Code make this even easier today.

How She Trained the AI

Andrea says the setup is the easy part. Tools like VAPI or Retell AI can spin up an AI receptionist quickly. The real work is training it to say the right thing every time.

So she listened to every call, found the problem spots, and updated the prompt to fix them.

Her big mindset shift was to think in steps and systems, and to train the AI like a junior employee.

If a client calls upset, the AI transfers the call to her. If a client wants an estimate, it books the visit on the calendar. Just two automations gave her back at least 20 hours a month.

Listed for Sale — and a $750,000 Offer

With calls handled and time back, they listed the company for sale. They also hired a friend Andrea had known for 20 years as operations manager in December 2024.

Around the same time, they got an offer of $750,000, well above their $470,000 purchase price.

They also bought a small fertilization and pest control company for $170,000, with the seller financing half.

In the end, they decided not to sell, since selling would leave them without an income source. The business was finally stable and running without them handling calls.

When It Fell Apart… Again

In January 2025, the family moved abroad for six months and left the manager in charge. But the business started sliding. Andrea had also stepped away in September 2025 to focus on her own AI company.

When they returned near New Year, their bank account had $2.50 in it. They discovered the manager, a friend of 20 years, had been stealing.

Five days later, a full truck of equipment worth $10,000 to $15,000 was stolen. The lesson Andrea took away was painful but clear: they had not learned how to lead a company.

Rebuilding Leaner with AI

They let the manager go. Good replacement managers wanted $100,000 or more a year, which the company couldn’t afford. So instead of hiring, they automated more.

Now Andrea’s husband goes to the office just one day a week for sales. AI handles the marketing, which brought in so many leads that May was their biggest month ever.

They also built a dashboard to track their real numbers:

which crews are efficient
how long jobs take
and pay versus what each client is charged

For people, they simply promoted their longest-tenured worker to organize the crews each morning. Andrea says missing those key numbers is exactly why they got robbed without noticing.

What Andrea Learned About Buying Businesses

Andrea’s top warning is to never buy a company unless the seller finances at least part of it, so they keep some skin in the game.

If the idea of owner financing appeals to you, Hannah Ingram did exactly that in Episode 571, buying an entire self-service car wash with the seller footing part of the bill.

Andrea also passed on another deal where clients paid three months late and visits were priced at $25, far below their $60 minimum.

In her own company, clients are billed on the first of the month, before any work is done. She warns that raising prices and changing terms after an acquisition will usually cost you those customers.

Tech/Tools

Here are the main tools Andrea mentioned:

Make – automation platform for connecting apps and building workflows
Jobber – CRM built for landscaping and cleaning services
Claude Code – tool she uses daily to build automations
VAPI and Retell AI – platforms for building AI phone receptionists
Upwork – where she hired freelancers to help build automations

Where the Business Is Now

Today the company is leaner and steadier. Andrea’s husband goes into the office about one day a week for sales, and they promoted their longest-tenured worker to organize the crews each morning. Last month the business did $75,000 with 7 employees.

What’s Next for Andrea?

These wins freed Andrea to build her own venture at AndreaPalacio.ai, where she helps other owners run an “AI-first company.”

She launched a program, Crewless, for business owners making that shift — mainly local services plus coaching and consulting.

You can find her on Instagram and YouTube. DM her the word “sidehustle” on Instagram for a personalized plan.

Andrea’s #1 Tip for Side Hustle Nation

“Don’t quit on your goals and dreams.”

Episode Links

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