Entry & Exit - Inside the Security & Fire Industry

Scaling a security business isn't just about hiring more people. It's about getting more out of the team you already have. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down how they're using international employees and AI agents at Alarm Masters to automate estimating, prospecting, sales support, and daily operations. They share what's working, wh...

Breaking $1M isn’t about working more. It’s about changing how you run the business. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down why security business owners often get stuck between $500K and $1M in revenue and what needs to change to push through that ceiling. They cover why taking too much cash out of the business can kill growth, how wearing every hat eventu...

Service might be one of the most undervalued revenue opportunities in the security industry. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down why they’re changing the way they think about service revenue inside Alarm Masters. After learning that 70% of another large security company’s revenue comes from service alone, they realized they may have been treating servic...

Going from $2 million to $12 million didn’t come from one big breakthrough. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble zoom out on the last three and a half years of growing Alarm Masters and break down the biggest drivers behind that growth. They explain why they stopped trying to hire “okay” people cheaply and started investing heavily in great people, why you need to...

Alarm Masters is expanding across Texas. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down two strategic acquisitions, their partnership with Platinum Technologies, and how they’re taking the growth playbook they built in Houston into North Texas. After three and a half years and 11 Houston-area acquisitions, they finally have a repeatable strategy for scaling throug...

The best lead source for your security business might be simpler than you think: get face-to-face with your customers. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down why in-person prospecting has become one of Alarm Masters’ most effective ways to generate project revenue. Service calls, coffee drops, and prospecting drop-ins account for 90% of their project reven...

Growing a security business gets harder when the financial side of the company can’t keep up. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down why Alarm Masters hired a Director of Finance and the lessons they learned as the business grew. They share their journey from handling the books themselves, to outsourced bookkeeping, to building the financial leadership nee...

AI employees aren’t the future; they’re already doing real work inside Alarm Masters. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down the digital employees they’ve built to handle estimating, prospecting, sales opportunities, operations, collections, and customer service. They explain how these AI agents work alongside their team, communicate with each other, and a...

Your salespeople should be selling, not spending half their week building proposals, updating the CRM, and scheduling appointments. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down how Alarm Masters is simplifying the sales role so reps can spend more time face-to-face with customers. They share how they're using international employees and AI to handle proposa...

Security companies can look incredible on paper; but not all recurring revenue is created equal. In this special collaborative episode of Entry & Exit , Jack from JackQuisitions breaks down the security industry and the 10 things he would evaluate before buying a security company or building one from scratch. From RMR quality and customer churn to contracts, licensing, service, and customer co...

The traditional alarm company is changing fast. In this episode of Entry & Exit , Stephen Olmon and Collin Trimble explain why independent alarm companies are facing increasing pressure from industry consolidation, evolving customer expectations, and the shift toward video and access control. They discuss why recurring monitoring revenue is no longer enough, how the industry's most succes...

Most business owners are still using AI like a smarter search engine. They're missing where the real leverage begins. In this episode of Entry & Exit , Stephen Olmon and Collin Trimble pull back the curtain on their AI journey, from using ChatGPT to clean up emails to building AI agents that automate complex workflows across their business. They explain the mindset shift that changed ever...

AI isn't coming for the security industry, but it is coming for companies that refuse to adapt. In this episode of Entry & Exit , Stephen Olmon and Collin Trimble explain why AI is becoming the biggest competitive advantage for security integrators. They discuss how operators can use AI to improve efficiency, protect margins, stay ahead of larger competitors, and why becoming "AI nat...

The best sales strategy might not come from your sales team. It might come from your service department. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down the playbook Alarm Masters uses to turn routine service calls into major commercial projects. They explain why leading with exceptional service builds trust faster than a sales pitch, how their teams work together...

Building a great service business requires more than hiring great technicians. It requires building the right leadership team. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble share how they've approached key leadership hires at Alarm Masters. They discuss when to hire directors, why operations is often the first bottleneck, and how to know when your business is ready for...

Difficult customers are inevitable. Losing great customers because you handled the situation poorly doesn't have to be. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down the systems they use to handle customer complaints, payment disputes, and difficult conversations without letting emotions get in the way. They discuss why the best operators separate business f...

Paying your sales team more sounds risky, until you realize it can actually make your business more profitable. In this episode of Entry & Exit , Stephen Olmon and Collin Trimble break down the compensation strategies that attract top-performing salespeople, drive better results, and help security companies scale. They discuss why most operators underpay their sales teams, the dangers of commi...

Paid ads can be one of the fastest ways to grow a security company—or one of the fastest ways to waste money. In this episode of Entry & Exit , Stephen Olmon and Collin Trimble break down the paid advertising channels security operators should actually be paying attention to. From Google PPC and Meta ads to LinkedIn campaigns and competitive intelligence, they discuss where they're invest...

IT Is Taking Over Security and Most Integrators Aren’t Ready. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble discuss one of the biggest shifts happening in the security industry: the rise of IT as the primary decision-maker. What used to be a facilities-driven purchase is rapidly becoming a technology conversation centered around APIs, cybersecurity, data ownership, interope...

Technology is changing fast, and the security industry is being forced to keep up. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble recap ESX and share their biggest takeaways from the conference floor. They discuss the growing interest in automation, the rise of new software providers, the importance of open APIs, and why some operators are moving faster than the rest of the...

Your technicians don't need to sell more, they need to collect better information. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble share how they're using AI to improve service operations at Alarm Masters. From automated technician workflows and smarter scheduling to uncovering new sales opportunities, they break down practical ways operators can increase efficiency...

Your sales team shouldn't be spending their time updating CRMs, building quotes, or chasing down information. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down the AI tools they're using at Alarm Masters to help their sales team do more with less. From automated quoting and proposal generation to meeting transcription, sales coaching, and CRM automation, th...

Everyone is talking about AI sales agents—but most of the hype doesn't match reality. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble share how they're actually using AI at Alarm Masters to find buying signals, generate leads, and automate parts of their outbound sales process. They break down the tools, workflows, and lessons they've learned while building AI-...

Growth solves a lot of problems—but it also creates new ones. In this Founder Series episode of Entry & Exit , Stephen Olmon and Collin Trimble share a candid update on Alarm Masters' growth in 2026. They break down what's driving record performance, the acquisitions they're pursuing, the operational improvements paying off, and the challenges they're still working through....

Most companies don’t stall because of bad strategy. They stall because they tolerate B players for too long. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down the hidden cost of hiring “good enough” talent — and why average employees quietly cap company growth, culture, and valuation. They unpack the lessons learned scaling Alarm Masters, including why A players mult...