Introduction
Today we’re diving deep into the world of entrepreneurship through acquisition with Sean Daly. After building and exiting multiple businesses from scratch, Sean took a different path – acquiring an established HVAC company and applying startup principles to drive growth. In this Q&A, he reveals how treating an acquisition like a startup with velocity, experimentation, and a bias for action can transform a traditional business.
Founder Success Story QnA
Give us a quick background on your zero to one years and how they led to your desire to buy a business
I’m a Miami guy born and raised. I went to school in Philly and made my way to New York. I got into tech right out of college and sort of wandered onto a rocket ship – a company called Gia Technologies (then called Sailfish Move). I was the first business development hire there. The company really took off – we sold software to the insurance sector. I was there for four great years and then moved down to Miami. Gia went on to become a unicorn and billion-dollar-plus valuation. After that experience, I joined a venture studio to build a business in title insurance called Expa Title. We weren’t looking to sell initially but ended up exiting to Real Brokerage, a public company, after raising venture money. Then I left Real Brokerage at the beginning of last year to go into entrepreneurship through acquisition and bought a business in July of last year.
How was the liquidity event when you exited to Real Brokerage?
It was a successful exit where everything worked out for all parties involved. I like to think that I did very well by my investors, and the company is still growing today. We’re providing successful roles and people are growing in those roles. I get to follow along with what they’re doing. It was satisfying looking back – it all worked out for everybody.
Why were you so interested in entrepreneurship through acquisition when you were thriving in zero-to-one land?
I fell in love with the idea of entrepreneurship. I don’t think entrepreneurship through acquisition and zero-to-one need to be mutually exclusive. There’s a good definition of entrepreneurship that resonates with me: being able to proceed with a business or an idea without regard for current resources. That’s a really good definition of entrepreneurship. There are different scales of that – there’s a more conservative approach which is entrepreneurship through acquisition, and there’s a more extreme version which is starting from scratch. I think I fell in love with the idea of being entrepreneurial. Both my parents were entrepreneurs – my dad had a successful software company in the late 90s, my mom had a successful marketing company, and my grandfather built a successful performing arts center in Miami. Being around that environment and just deciding I’m going to do this despite people telling me it’s a bad idea is what I enjoy.
Tell us about your search process for finding a business to acquire
Understanding sales and outreach, I gave myself a one-year runway to make it happen after talking with my wife. I treated it like jumping off a cliff and building the plane on the way down, so I needed to move quickly. I hired an individual from Ukraine on Upwork to help source deals through cold outreach. We emailed businesses primarily focused on home services – that’s the space I really know from title insurance. Home services businesses kind of taste like chicken; they all operate in similar fashions. I focused on home services because I understood that sector. We went through about 300-400 businesses in the first few months, which is more than a typical PE firm does in a year. This velocity helped me build rhythm – by the time I had my first diligence call with a roofing company in Orlando, I knew what to ask because I’d had so many conversations.
How many businesses did you actually contact during your search, and what was your response rate?
I sourced thousands of businesses. I looked at about 3-400 with seriousness, had probably 50+ conversations with companies, sent out a few LOIs, was close to one I didn’t pull the trigger on, and found the business I bought in month four. One conversation that helped me was with an active searcher who said there are three levers: location of the business, size of the business, and industry. You have to pick two to be successful. I was flexible on all three initially because I’d managed remote teams before, which allowed me to look at more businesses.
What messaging did you finally settle on for your outreach, and how much did your outreach assistance cost?
We used a mixture of reaching out to brokers and direct campaigns to owners. The consistency was key – every morning I’d meet with my assistant and review messages sent, broker calls, and everything else. We followed up consistently, which gave us a good chance. She was getting paid about $10 an hour, so roughly $1,600 a month. When you incorporate opportunity cost – if you’re giving up a year versus two years of running a business and bringing in salary – the decision was better to hire somebody and move faster than to do it all myself.
How do you justify the cost of search assistance when many searchers recoil at $1,000-$2,000 a month?
It’s all about opportunity cost. If you’re going to buy a business that will pay you a salary conservatively at $100,000 a year, that’s about $8,500 a month. For every month that goes by without a business, you’re effectively losing that opportunity cost. Paying $1,000-$2,000 a month to pull forward by many months a salary of $8,500 a month is an enormous ROI. Entrepreneurs aren’t just risk-takers – the best entrepreneurs are risk reducers who balance risk and reward well. If you’re making decisions based purely on capital, it’s better to do it than not.
What deal did you finally acquire, and how did you structure it?
I bought a small HVAC business in Coral Springs, Florida. I hit it off with the founder who’s from the Dominican Republic (like my wife), and we shared similar family values. The business was doing about $1.5 million in revenue over the last three years with almost $200,000 in net income. They had about nine employees, an office location, and five trucks. It was 27 years old with thousands of customers who kept coming back, but they didn’t pay attention to their online presence – Google rating was only 4.3. I bought the business for $700,000 – $630,000 in cash and a $70,000 seller note. I did this for competitive reasons since the seller had deals fall through with SBA financing before and didn’t want to deal with it again.
What operational changes did you implement immediately after acquisition, and would you do anything differently?
I wouldn’t change anything because if you make mistakes along the way, it’s okay as long as you’re learning from them. We transitioned to a new back office system in about a week and a half – it was painful for about a month, but 30 days later it was fine. I think it’s better than trying to transition over a year. We began offshoring back office activities to Nicaragua – permitting, HR, and we tried inbound calls too. The permitting and HR worked very well, but the inbound calls didn’t work because homeowners had nuanced questions that required technical knowledge. We built a sales team in Nicaragua with four people – one handling estimations and service agreements (the company had none when I started), which worked extremely well. We closed a $4,000 change-out we definitely wouldn’t have gotten otherwise. We also tried cold outreach with two other people making 100+ calls per day, but had to shut it down after 45 days because our cost per lead was over $1,000.
How did your team react to all these rapid changes, and how did you manage that chaos?
It’s all about how you handle it. At the end of the day, you own the business now and will run it how you feel is best. There will be some people that might fall through, but that’s okay. What’s important is handling it the right way. For example, when we transitioned off punch cards to a digital system, one technician refused to use the new system. I threw the punch system in the trash and told him it was his last day. If you believe what you’re doing is the absolute best thing for the business – not ego-driven – it makes it easier to have conversations internally. You can say: ‘I’m doing this because of this, that, and that reason.’ At the end of the day, I take feedback from everyone, but I’m going to do what I think is best. It’s important there’s one person defining the direction.
How has your background prepared you to handle these leadership challenges, especially when many searchers have never managed a team before?
It takes a while to learn these things – I’ve definitely gotten burned and understand what it’s like to be on the other side too. I’d rather give someone a bullet to the head than aid to the chest – if I were sitting on the other side, I’d just want clarity. You learn this stuff over time. For searchers, you’re definitely going to learn it one way or another. Honestly, I love business. The challenge every single day of making mistakes – I’ve gotten to the point where I literally like messing up and bouncing back. It’s all about how quickly you bounce back. Facing the challenge of every single day is what makes the whole process exciting. As an exited founder, it really is the journey that is the destination – enjoy the process and learn.
How has the business performed since you took over, and what’s your growth strategy?
The business is on track to grow 20-30% over the next six months, and I’d like to see that grow significantly more over 2025. Our net income has stayed steady despite all the changes and mistakes we’ve made. Every business is incredibly challenging with industry-specific challenges – this one has cash flow challenges and team challenges. I’m totally okay not growing 400% year-over-year unsustainably to make sure we have the right foundation and direction, because over the long run it’s going to make that much more of a difference. I feel very good about where we’re going. Every day is incredibly challenging and exciting – I have no idea where the train is going, but that’s part of the fun.
Sean Daly Business Stats
Sean acquired a 27-year-old HVAC business that had established itself in the home services market but needed modernization and strategic growth initiatives. Here are the key business metrics from when he took over:
- Annual revenue: $1.5 million
- Annual net income: ~$200,000
- Employees: 9 staff plus 5 service trucks
- Customer base: Thousands of loyal customers from 27 years in business
- Acquisition price: $700,000 ($630,000 cash, $70,000 seller note)
- Current growth trajectory: 20-30% over next 6 months
| Key Metric | Value |
|---|---|
| Business Age | 27 years |
| Revenue (Annual) | $1.5M |
| Net Income (Annual) | $200,000 |
| Employees | 9 |
| Acquisition Price | $700,000 |
| Current Growth Rate | 20-30% (6-month projection) |
Sean Daly Method
Sean applied startup methodology to his acquisition with remarkable speed and focus. These are the core elements of his approach to transforming the business:
- Treated the acquisition like a startup from day one with rapid experimentation
- Implemented new back office system in just one week instead of a year-long transition
- Offshored back office functions (permitting, HR) to Nicaragua for cost efficiency
- Built offshore sales team focused on estimates and follow-up rather than on-site selling
- Set aggressive revenue targets (300%+ return on ad spend) with rapid testing cycles
- Maintained urgency with artificial deadlines to accelerate progress
- Accepted that some experiments would fail but learned quickly from each one
Sean Daly Tools
Sean strategically implemented tools that enabled rapid scaling while maintaining cost discipline. He focused on systems that could be quickly learned by his offshore team while providing maximum impact on operations and growth:
- New back office system – Replaced whiteboards and punch cards with digital workflow management in just one week
- Nicaraguan offshore team – Cost-effective sales and back office support ($10/hour) that scaled operations without large fixed costs
- Structured pricing templates – Enabled non-technical sales staff to accurately estimate jobs using technician input
- Google Ads – Primary digital marketing channel with carefully monitored ROAS targets
- Rigorous financial tracking – Focused on cost per lead and return on ad spend to quickly kill unprofitable channels
Key Notes
These insights capture Sean’s most valuable lessons from applying startup principles to business acquisition. They represent the mindset shifts and tactical decisions that made his approach successful:
- Opportunity cost of search time dwarfs assistance costs – $1,600/month help saves $8,500/month in delayed income
- Rapid technology transitions (1-2 weeks) create short-term pain but long-term gain versus year-long migrations
- Sales doesn’t require deep product knowledge – structured processes and relentless follow-up matter more
- Front desk/customer service needs industry knowledge that can’t be easily offshored
- Decisive leadership matters more than perfect decisions – move quickly and adjust course
- Every business has 2-4 year compounding cycles where consistent effort produces breakthrough results
Get Started in Just 5 Steps
Sean’s approach demonstrates how to implement a startup mindset in business acquisition. Follow these five steps to apply his methodology to your own search:
- Define your three acquisition levers (industry, size, location) but be flexible on at least two to increase deal flow
- Invest in search assistance – the opportunity cost of slower search far exceeds the $1,000-$2,000 monthly cost
- Create artificial urgency with tight deadlines (e.g., ‘find a deal in 60-90 days’) to accelerate progress
- Structure deals to close quickly – avoid SBA if seller has negative experiences with it
- After acquisition, immediately implement 2-3 key changes that can be rolled out in weeks, not months
Conclusion
Sean Daly’s journey proves that entrepreneurship through acquisition doesn’t mean maintaining the status quo. By applying startup principles of velocity, experimentation, and rapid iteration, he’s transforming a traditional HVAC business into a growth machine. His approach – treating acquisition like building a startup with urgency and decisiveness while building for long-term compounding – offers a powerful model for aspiring entrepreneurs. The key takeaway? Don’t just buy a business – acquire a platform for innovation where you can move fast, make mistakes, and learn quickly while building something lasting.