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. 2d ago ·  Video

    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 decision-maker. What used to be a facilities-driven purchase is rapidly becoming a technology conversation centered around APIs, cybersecurity, data ownership, interoperability, and AI. They break down why open APIs are becoming table stakes, how enterprise buyers are evaluating security vendors differently, and why security professionals who can't speak the language of technology risk being left behind. The conversation also explores cybersecurity vulnerabilities, penetration testing, AI's impact on enterprise security, and practical ways integrators can future-proof their businesses. In this episode: → Why IT is becoming the economic buyer in security projects  → The growing importance of APIs, integrations, and data ownership  → Why open platforms are winning over closed systems  → How AI is accelerating change across the security industry  → Cybersecurity risks every integrator should understand  → Why penetration testing is becoming more common  → The future of custom-built security software stacks Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

    18 min

  2. 4d ago

    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 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 industry. They also break down what stood out from conversations with vendors, manufacturers, and fellow operators, plus where they see the industry heading over the next few years. In this episode: → Key takeaways from ESX 2026 → How the conference compares to ISC West → Why open APIs are becoming more important → The rise of new software providers in security → A business idea for a unified security platform Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

    17 min

  3. Jun 12 ·  Video

    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 automated technician workflows and smarter scheduling to uncovering new sales opportunities, they break down practical ways operators can increase efficiency and profitability. In this episode: → Capturing better field data with AI → Automating technician notes and workflows → Improving scheduling density and utilization → Predicting job duration with historical data → Turning service calls into future sales opportunities → Why technician selling is the wrong goal Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

    19 min

  4. Jun 10 ·  Video

    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 help their sales team do more with less. From automated quoting and proposal generation to meeting transcription, sales coaching, and CRM automation, they share practical ways operators can eliminate busywork and give salespeople more time to sell. In this episode: → Building AI-powered quoting and proposal workflows → Using Claude and custom GPTs to save hours on estimates → Recording meetings and capturing action items automatically → Creating sales playbooks with Notion AI → AI-powered onboarding and training opportunities → Real-time sales coaching with Dialpad → Automating CRM updates and reducing admin work → How operators can improve sales productivity today Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

    16 min

  5. Jun 5 ·  Video

    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, generate leads, and automate parts of their outbound sales process. They break down the tools, workflows, and lessons they've learned while building AI-powered systems that create real sales opportunities. In this episode: → Why most AI SDR claims are overhyped → Finding buying signals with public data → Building AI-powered lead generation workflows → Automating prospecting and outreach → Tools and tactics operators can use today Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

    19 min

  6. Jun 3 ·  Video

    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 driving record performance, the acquisitions they're pursuing, the operational improvements paying off, and the challenges they're still working through. From sales maturity and AI adoption to accounting headaches and inventory management, this is an inside look at what it actually takes to scale a service business. In this episode: → How Alarm Masters is growing through acquisitions and organic sales  → The sales lessons improving close rates and deal quality  → Why operational discipline is creating better customer outcomes  → The realities of GAAP accounting and preparing for an eventual exit  → The role AI is playing across the business  → The biggest challenges still ahead in 2026  → What’s next for expansion into new markets Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

    18 min

  7. May 29 ·  Video

    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 — and why average employees quietly cap company growth, culture, and valuation. They unpack the lessons learned scaling Alarm Masters, including why A players multiply output across the business, how mediocre hires increase founder dependence, and the mindset shift that changed how they recruit leadership talent. The conversation dives into hiring psychology, identifying true high performers, why process alone can’t compensate for weak talent, and the operational ripple effects of building a team stacked with A players. Inside this episode:  → Why B players often create more work for founders  → The difference between A, B, and C players  → Why process can’t turn average talent into elite talent  → The real opportunity cost of mediocre hires  → How A players improve every department around them  → Why hiring cheap talent slows company growth  → The impact of talent on enterprise value and acquisitions  → How to identify A players in the first 90 days  → Why top performers want to work with other top performers 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

  8. May 27 ·  Video

    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 leadership hires that changed the company, the painful acquisition lessons they learned, and why investing ahead of growth became their biggest advantage. They share why A players outperform entire teams of average talent, how building stronger operational structure transformed the business, and the acquisition mistakes that forced them to rethink diligence, integration, and growth strategy. Inside this episode: → Why one A player outperforms two B players → Hiring a sales manager earlier than expected → Building accountability and structure across operations → What great operators actually do differently → The importance of humility in leadership hires → Lessons learned from successful and failed acquisitions 🔗 More Entry & Exit — https://www.entryandexit.co/ Connect:  Stephen Olmon — http://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

    17 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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