Entry & Exit - Inside the Security & Fire Industry

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...

Most operators think scaling comes down to process. But the real unlock is talent. In this episode of Founder’s Story , Stephen Olmon and Collin Trimble break down the lessons from year two of operating Alarm Masters — including the leadership hires that changed the company, the painful acquisition lessons they learned, and why investing ahead of growth became their biggest advantage. They share w...

Most businesses don’t stall because of strategy. They stall because everything depends on the owner. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down the hidden cost of founder dependency — why owners become the bottleneck, how it limits growth, and what eventually breaks when every decision runs through one person. They share lessons from scaling Alarm Masters, emp...

Most business acquisitions don’t fail because of strategy. They fail because operators underestimate hiring, systems, and execution.  In this episode of Entry & Exit: Founder’s Story , Stephen Olmon and Collin Trimble break down the first full year running Alarm Masters after the acquisition — including the wins, the mistakes, and the operational changes that completely transformed the company...

Most security companies are still marketing like it’s 2015. The best operators are already adapting to AI search, modern SEO, and smarter outbound systems. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down the marketing channels driving real growth for security companies today — from Google reviews and local SEO to AI optimization, outbound prospecting, and commercia...

Most people dream about buying a business. The first 90 days show you what ownership actually feels like. In this episode of Entry & Exit: Founder’s Journey , Stephen Olmon and Collin Trimble break down the chaotic first three months after acquiring Alarm Masters — from stolen equipment and blacklisted domains to learning every role inside the company. They share the real lessons from stepping...

AI won’t replace your team — but it will make them dramatically more effective. In this episode of Entry & Exit , Stephen Olmon and Collin Trimble break down how they’re using AI to scale a security business — from simple tools like ChatGPT to fully deployed agents handling quoting, support, and operations. From custom GPTs for sales and tech support to an estimation agent that turns plans int...

In this episode of Entry & Exit — part of the Founders Story Series, Stephen Olmon and Collin Trimble walk through how they went from software and small business experiments to acquiring their first security company — and why the industry checked every box they were looking for. They break down the real drivers behind their decision: recurring revenue, regulatory moats, fragmentation, and the...

Most trades sell one thing. Security sells four — and that changes everything. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down why the security industry is uniquely built for high-ticket sales — and how operators turn small jobs into $50K–$100K+ projects. They unpack the core advantage: multi-scope selling across fire alarm, intrusion, video, and access control — p...

A security business doesn’t just grow one way — it’s built through smart expansion, whether that’s buying, building, or blending both. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down the real tradeoffs between greenfielding a new location and acquiring an existing company in the security industry. From capital requirements to operational complexity, they walk throu...

$100K Security Installs: Where the Money Actually Goes Burglar alarms aren’t the whole story anymore—and they’re definitely not $100K. In this episode of Entry & Exit , Stephen Olmon and Collin Trimble break down what actually makes up a six-figure security installation—and why the real money is in multi-scope projects. From cameras and access control to fire and intrusion, they walk through h...

Sales isn’t about talking more—it’s about understanding why people say yes. In this episode of Entry & Exit , Stephen Olmon and Collin Trimble break down the sales psychology behind closing high-ticket deals—especially in industries where trust, risk, and certainty matter most. They challenge the idea that great salespeople are extroverts, unpack why emotional intelligence beats raw IQ, and ex...

​​ Burglar alarms aren’t dead—but they are being replaced. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down how AI, video, and access control are reshaping the security industry—and why traditional alarm systems are losing value. They cover what’s driving the shift, how security stacks are consolidating around video, and what operators need to do to stay competitive...

If you’re building a security business, the biggest mistake isn’t picking the wrong tools—it’s building a stack that doesn’t scale. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down the ultimate “god mode” security stack—and how your tech choices impact growth, operations, and enterprise value. From RMR to vendor selection, they share what actually works (and what do...

If you’re in the security or life safety industry, the biggest shift happening right now isn’t incremental—it’s foundational. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down the biggest takeaways from ISC West, including the rapid acceleration of AI, the rise of startups, and what it all means for operators, monitoring companies, and the future of the industry. Fro...