Entry & Exit - Inside the Security & Fire Industry

Stephen Olmon and Collin Trimble
  • 5.0 (7)
  • ENTREPRENEURSHIP

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.

  1. 22H AGO

    How We Bought a Security Company (And Why It Was the Perfect Industry)

    In this episode of Entry & Exit, 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 opportunity to scale through acquisition. From discovering the “buy vs. build” path to finding the right deal (on the first try), this is a candid look at how their journey into security actually started — including what they got right, what they missed, and what almost killed the deal. If you’ve ever considered buying a business — or wondered why security continues to attract serious operators — this episode gives you the full origin story. Inside this episode:  → Why security stood out vs. HVAC, plumbing, and other trades  → The role of recurring revenue in making the model work  → How regulation and licensing create a competitive moat  → Finding and closing on their first deal (Alarm Masters)  → Mistakes they made during diligence and legal process  → How they financed the acquisition with an SBA loan 🔗 More Entry & Exit — https://entryandexit.com Connect:  Stephen Olmon — http://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

    20 min

  2. 5D AGO

    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 operators turn small jobs into $50K–$100K+ projects. They unpack the core advantage: multi-scope selling across fire alarm, intrusion, video, and access control — plus the “fifth scope” that expands deals even further. From real-world deal breakdowns to the compounding power of recurring revenue, this episode shows why security isn’t just another trade — it’s a sales engine. Inside this episode:  → The 4 core scopes that drive high-ticket security deals  → Why security problems grow (and lead to bigger contracts)  → How a $35/month account can turn into a $75K project  → The role of urgency, regulation, and risk in closing deals  → Why recurring revenue is the “eighth wonder of the world” 🔗 More Entry & Exit — httpsentryandexit.com Connect: Stephen Olmon — http://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

    15 min

  3. APR 29

    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 between greenfielding a new location and acquiring an existing company in the security industry. From capital requirements to operational complexity, they walk through what actually drives success — and why the best operators don’t treat this as an either/or decision. They dig into the realities of starting from scratch vs. buying a platform, how to think about risk, and why having a repeatable playbook matters more than the strategy you choose. Plus, they unpack a hybrid approach that combines both tactics to scale faster and smarter. Inside this episode: → Greenfield vs. acquisition — the real pros and cons of each → Why having a playbook is the difference between scaling and stalling → The hidden risks (and advantages) of starting from scratch → How to test a new market before going all-in → The hybrid strategy: combining buy + build for maximum optionality 🔗 More Entry & Exit — entryandexit.com Connect:  Stephen Olmon — http://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

    16 min

  4. APR 24

    $100K Security System Breakdown: Cameras, Access Control & More

    $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 how modern security stacks are built, sold, and scaled—and why bundling multiple systems is the key to bigger deals and long-term revenue. They also unpack real-world project economics, margins, and what separates a $20K job from a $150K+ install. In this episode:  What a $100K security project actually includes  The “big four”: video, access, fire, and intrusion  Why multi-scope selling drives massive deal size  How camera systems and specialty hardware boost margins If you’re in security, HVAC, or home services, this is a tactical breakdown of how to think bigger—and sell smarter. More Entry & Exit — https://www.entryandexit.co/ 🔗 Connect Stephen OlmonCollin Trimble  Owned and Operated New Episodes Every Wednesday! Subscribe For More

    15 min

  5. APR 22

    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 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 explain how top performers position themselves as the “safe choice” in high-stakes decisions. From uncovering real buyer motivations to building authority and confidence, this episode is a tactical deep dive into what actually drives deals across the finish line. In this episode:  Why high-ticket sales is driven by emotion—not logic  The role of fear, risk, and “playing it safe” in buying decisions  How to uncover what really matters to your customer  Why “What’s your biggest pain point?” is the wrong question If you sell anything high-value—or want to—this is your playbook for closing with confidence. More Entry & Exit — https://www.entryandexit.co/ 🔗 Connect Stephen Olmon Collin Trimble  Owned and Operated New Episodes Every Wednesday! Subscribe For More

    14 min

  6. APR 17

    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 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. In this episode: Why alarms are being “demoted”How AI-powered cameras are changing securityThe shift from alarms as triggers to validatorsWhy DIY systems are compressing valueHow to use alarm accounts to upsell higher-value servicesIf you’re in the security or service space, this is your playbook for what’s next. More Entry & Exit — https://www.entryandexit.co/ Owned and Operated New Episodes Every Wednesday! Subscribe For More

    14 min

  7. APR 15

    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” 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 doesn’t) when building a modern security business. They cover:  Why every sale should include recurring monthly revenue (RMR)  The tradeoff between upfront cash and long-term value  Why too many vendors create operational drag  The importance of unified platforms across security systems  Why cybersecurity and reliability matter more than features  The exact stack they use (Brivo, Eagle Eye, DMP) and why If you run a security or life safety business, this episode will help you build a scalable, high-value operation.  More Entry & Exit — https://www.entryandexit.co/ Owned and Operated New Episodes Every Wednesday! Subscribe For More

    16 min

  8. APR 8

    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 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. From AI-powered video monitoring to fully autonomous agents replacing operators, they unpack where things are actually headed—and what’s already changing today.  They explain why legacy players may be too late to the cloud shift, how AI is reshaping video surveillance into the core of the security stack, and why pricing pressure and automation could disrupt traditional monitoring models. Whether you attended ISC West or not, this episode gives you a clear picture of where the industry is going next—and who’s at risk of getting left behind. They cover:  Why AI dominated ISC West—and what that really means for operators  The shift from alarms to video as the core security solution  How AI agents are replacing human monitoring operators  Why video monitoring pricing is under pressure If you run a security, fire, or service business, this episode will help you understand where the industry is heading, what trends actually matter, and how to prepare for the next wave of change. More Entry & Exit — https://www.entryandexit.co/ Owned and Operated New Episodes Every Wednesday! Subscribe For More

    16 min
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Ratings & Reviews

5
out of 5
7 Ratings

About

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.

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