Entry & Exit - Inside the Security & Fire Industry
Entry & Exit is a podcast about building, scaling, and exiting security and fire businesses. Hosts Stephen Olmon and Collin Trimble share their journey growing Alarm Masters through acquisitions and organic growth, along with the lessons they’ve learned along the way.
From recurring revenue strategies to sales, operations, and M&A, Entry & Exit gives business owners and entrepreneurs an inside look at what it takes to succeed in the security industry. Whether you’re starting your first company, growing past the owner-operator stage, or thinking about an eventual exit, you’ll find practical insights and real stories to guide your path.
Episodes
49 episodes
When to Fire a Customer (And When to Fight for Them)
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 custom...
Why Paying Salespeople More Makes Security Companies More Profitable
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 att...
The Security Industry's Best Lead Generation Channel Right Now
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...
Security Is Becoming an IT Business. Here's Why
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 decisi...
Our Biggest Takeaways from ESX 2026
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 t...
AI for Service Teams: Scheduling, Notes & More Revenue
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 autom...
AI Tools That Make Sales Teams More Productive
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 ...
AI SDRs Are Overhyped: How We Actually Use AI to Generate Leads
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, gener...
How We’re Growing EBITDA, Expanding Markets, and Fixing Bottlenecks
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 drivi...
The Hidden Cost of Hiring B Players
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 —...
The Biggest Lessons From Our Second Year as Owners
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...
Why Your Business Depends Too Much on You
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 becom...
How We Grew an Acquired Business 60% in Year One
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 brea...
Security Company Marketing That Actually Works in 2026 (SEO, AI & Lead Generation)
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 t...
Founder’s Journey: The First 90 Days After Buying a Business
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 m...
How to Scale Your Business with AI (Without Replacing Your Team)
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 ...
How We Bought a Security Company (And Why It Was the Perfect Industry)
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 i...
Why Security Is the Perfect Industry for High-Ticket Sales
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 op...
Greenfield vs. Acquisition: How to Scale a Security Business the Smart Way
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 bet...
$100K Security System Breakdown: Cameras, Access Control & More
$100K Security Installs: Where the Money Actually GoesBurglar 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 ...
How to Close High-Ticket Deals Using Sales Psychology
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 indu...
Why Burglar Alarms Are Dying (And What’s Replacing Them)
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 traditi...
The Exact Security Tech Stack We’d Use to Scale to $10M
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” s...
Is AI Replacing Security Operators? (ISC West Breakdown)
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 ...
The Exit Playbook: How to Structure a Business Sale for Maximum Value
If you’re thinking about selling your security or life safety business, the biggest mistake isn’t timing—it’s misunderstanding your options.In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down ...