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Entry & Exit - Inside the Security & Fire Industry

Stephen Olmon and Collin Trimble

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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  • 21 episodes
  • weekly
  • Avg 15 min
  • English

Episodes 21

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  • Yesterday · 13 min

    Hiring an AI Developer: The Next Step in Business Automation

    Is hiring a full-time AI developer the next step in scaling a business? In this episode of Entry & Exit, Stephen Olmon and Collin Trimble share why they hired a dedicated AI developer at Alarm Masters and how they're using AI agents to automate business operations, improve efficiency, and reduce costs. They break down the three priorities behind their AI strategy: building secure infrastructure, managing AI costs with local language models, and developing custom AI agents that solve real business problems. From automating billing and accounts receivable to improving customer service, lead generation, and technician support, this episode explores what it takes to move beyond basic AI tools and build automation that delivers measurable results. Discover how businesses can use AI to scale operations, free up employee time, and create more efficient systems without replacing their teams. ━━━━━━━━━━━━━━━━━━━━ WHAT YOU'LL LEARN: Hiring an AI Developer: Why Alarm Masters invested in a full-time developer to accelerate its AI strategy. AI Infrastructure & Security: Building reliable automation systems while protecting business and customer data. Reducing AI Costs: Managing token expenses and using local AI models to reduce operating costs. AI Agents for Business: Automating billing, accounts receivable, customer communication, and sales workflows. The Future of Business Automation: Exploring voice AI agents, technician support, and human-in-the-loop systems. ━━━━━━━━━━━━━━━━━━━━ CONNECT WITH ENTRY & EXIT: Website & Newsletter: https://entryandexit.co Stephen Olmon: https://x.com/stephenolmon Collin Trimble: https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E66
    October 28 · 14 min

    The Business Metrics We Wish We Tracked Sooner

    If you’re not tracking the right numbers, you’re leaving money on the table. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down the key performance indicators (KPIs) every service business owner should be tracking to improve efficiency, increase revenue, and scale operations. Using real examples from Alarm Masters, they explain how technician utilization, sales pipeline conversion, and customer retention directly impact profitability. They also share the overlooked metrics that helped them identify problems, set better goals, and make smarter business decisions. In this episode: The most important KPIs for growing a service business Tracking technician utilization, service revenue, and return trips Measuring sales pipeline generation and conversion rates Setting revenue goals and quotas across your team Why customer retention and first-call resolution matter Using data to identify inefficiencies and missed revenue How to start tracking KPIs without expensive software Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E65
    October 21 · 14 min

    Scaling From $1M to $10M: Leadership, Technology, and the Systems That Drive Growth

    The difference between a $1 million business and a $10 million business isn't just revenue. It's how the entire company operates. In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down what actually changes as a security business scales from $1M to $10M in revenue. Drawing from their experience building Alarm Masters, they discuss why leadership, technology, and smarter investments become critical as a company grows. They also explain how to escape the owner bottleneck, automate manual workflows, and build a sales team capable of supporting the next stage of growth. In this episode: → The biggest differences between a $1M and $10M business → Building a leadership team that removes the owner bottleneck → Why your technology needs to evolve as you scale → Automating manual tasks to improve efficiency → Shifting from daily operations to strategic investments → Using financial models to make smarter growth decisions → Why over-hiring salespeople can protect revenue targets Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E64
    October 14 · 15 min

    The New Playbook for Scaling a Security Business With AI

    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, where human oversight still matters, and how to build systems that support growth without unnecessary overhead. In this episode: → Freeing up salespeople to focus on selling → Combining international employees with AI automation → Automating proposals, prospecting, and appointment setting → Building AI agents that communicate and work together → Streamlining service quotes, customer follow-ups, and operations → Why AI still needs human oversight → Building the systems and infrastructure to support growth Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E63
    October 7 · 15 min

    The Blueprint to Break $1M in Your Security Business

    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 eventually becomes a bottleneck, and why owners need to protect their time for sales and business development. They also share how they’ve used time blocking, subcontractors, and international team members to create leverage without building a massive payroll. In this episode: → Why businesses get stuck below $1M → Reinvesting cash instead of increasing your lifestyle → Getting the owner out of low-value work → Prioritizing sales over service and installation → Using time blocking to protect growth activities → When to use subcontractors instead of hiring → Using international talent to handle back-office work → What the owner should still be doing personally → A simple blueprint for breaking through $1M Connect: Stephen Olmon — https://x.com/stephenolmon\ Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E62
    September 30 · 14 min

    80% of Our Leads Come From Service: What We’ve Been Missing

    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 service as a path to bigger projects instead of a major growth opportunity on its own. They explain how service calls can create revenue, strengthen customer relationships, and uncover larger project opportunities. They also lay out their plan to build a real sales process around service, proactively work their existing customer base, and pursue new customers through service first. In this episode: → Why they’ve been undervaluing service revenue → How 80% of their recent leads came from the service department → Why service needs its own sales process → Turning small service calls into larger project opportunities → Finding more revenue inside your existing customer base → Using proactive service to stay in front of customers → Winning new customers through service first → Alarm Masters’ goal to 4X service revenue next year Connect: Stephen Olmon — https://x.com/stephenolmon\ Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E61
    September 23 · 20 min

    How We Grew a Security Company From $2M to $12M

    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 hire ahead of the growth you want, and how the right technology and infrastructure can determine whether your business is actually ready to scale. Stephen and Collin also break down how they built a scalable sales team using data, specialized roles, international talent, and technology, plus why acquisitions have become a critical part of their strategy for reaching the next stage of growth. In this episode: → How Alarm Masters grew from $2M to $12M → Why great people are worth paying more for → Hiring ahead of the growth you want → Building a tech stack that can scale with the business → Using data to build a scalable sales team → Why sales reps shouldn’t be doing everything themselves → Using international talent and technology to increase production → How acquisitions accelerated Alarm Masters’ growth Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E60
    September 16 · 13 min

    We Made 11 Acquisitions. Here’s the Playbook That Finally Worked

    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 through M&A, sales, service, and RMR growth. In this episode: → Expanding Alarm Masters across Texas → Lessons from 11 acquisitions → Building a repeatable M&A and growth playbook → Scaling sales into North Texas → Growing service and recurring revenue → Why business gets easier at scale Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E59
    September 9 · 15 min

    The BEST Lead Source for Security Companies

    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 revenue, outperforming the digital and outbound channels most companies focus on. They explain how to make in-person prospecting scalable by using customer data, public information, and AI to identify buying signals before a salesperson ever walks through the door. They also share how to choose the right prospects, improve your pitch through repetition, and turn a simple drop-in strategy into a repeatable sales engine. In this episode: → Why face-to-face prospecting is their best lead channel → How service calls, coffee drops, and prospecting generate opportunities → Why salespeople should run 20–25 face-to-face appointments per week → Using AI and public data to identify buying signals → Finding the events that actually cause customers to buy → Improving your script, target contact, and offer through repetition → Turning in-person prospecting into a scalable sales system Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E58
    September 2 · 15 min

    Why Every Growing Security Business Needs a Finance Leader

    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 needed to support acquisitions, debt, budgeting, and long-term growth. In this episode: → When a business needs financial leadership → The difference between accounting and finance → Moving from cash to accrual accounting → Financial mistakes they made while scaling → Why acquisitions require stronger financials → Budgeting, forecasting, and managing cash flow → Managing for growth vs. managing for earnings → What to look for when hiring a finance leader Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E57
    August 26 · 18 min

    How AI Agents Are Changing the Way We Run Our Business

    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 automate tasks that used to require multiple handoffs. They also share where AI still needs human oversight and why voice-based agents could be the next major step for service businesses. In this episode: → Building AI employees that do real work → Automating estimates and prospecting with Eddie and Stu → Using Kevin to uncover missed customer demand → How AI agents communicate and complete workflows together → Automating operations, case management, and collections → Where humans still need to stay in the loop → The future of voice-based AI employees Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E56
    August 19 · 19 min

    How We Make Our Sales Team More Productive (And How You Can Too)

    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 proposals, prospecting, appointment setting, and follow-up; and why removing these tasks can create a more consistent pipeline. In this episode: → Why salespeople are wasting up to half their day → The tasks Alarm Masters removes from its sales reps → Using AI and international employees to support sales → Why they target 25–30 meetings per rep each week → The first two sales tasks they'd delegate Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E55
    August 12 · 9 min

    Should You Buy or Build Your First Security Company?

    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 concentration, Jack explains what actually makes a security business valuable and sellable. If you're considering entering the security industry through acquisition or starting from zero, this episode lays out what to look for—and the biggest mistakes to avoid. In this episode: → What makes security RMR valuable → Commercial vs. residential security → Contracts, churn, and customer concentration → Licensing and service department risks → What to evaluate before buying → Why you should buy the system, not just the revenue Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Jack Carr — https://www.youtube.com/@Jackquisitionsco Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E54
    August 5 · 14 min

    Why Traditional Alarm Companies Are Dying

    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 successful companies are adapting, and what security businesses need to do to stay competitive. They also explore the rise of modern security integrators, the operational changes required to scale, and why acquisitions are creating one of the biggest growth opportunities in the industry. If you own or operate a security company, this episode is a practical look at where the industry is heading,and how to prepare for what's next. In this episode: → Why independent alarm companies are being consolidated → How video and access control are replacing the traditional alarm model → The difference between an alarm company and a security integrator → Why recurring monitoring revenue is no longer enough → Building a scalable service and sales strategy → Using acquisitions to accelerate growth → How to cross-sell your existing customer base → Why the age of your customer base could become a major risk → The operational changes security companies need to make to survive the next decade Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E53
    July 29 · 20 min

    From ChatGPT to AI Agents: How We're Using AI to Transform Our Business

    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 everything, why treating AI like a digital employee unlocks entirely new possibilities, and how consolidating data inside Salesforce became the foundation for meaningful automation. They also break down the difference between simple automations and true AI agents, share how they built their own open-source AI stack without a software engineering background, and discuss the practical tools they're using today to create operational leverage. Whether you're just getting started with AI or looking to move beyond basic prompts, this episode offers a practical look at what's possible today. In this episode: → How Stephen and Collin went from AI skeptics to daily users → Why AI should be treated like a digital employee—not a chatbot → The importance of centralizing business data before adopting AI → The difference between automation and agentic AI → Building AI agents without a software engineering background → The open-source tools powering their AI workflows → How AI is helping automate sales, operations, and data analysis → Why the best time to start experimenting with AI is now Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E52
    July 22 · 15 min

    AI Won't Replace Security Companies. But It Will Change Them.

    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 native" is no longer optional. They also share the simplest way to start implementing AI in your business today. In this episode: → Why AI won't replace security companies—but will reshape the industry → The biggest mistake operators are making today → Why smaller companies have an advantage over larger competitors → How AI will impact margins and growth → The easiest way to start using AI in your business Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E51
    July 15 · 12 min

    Your Service Department Is Your Best Salesperson

    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 to create new opportunities, and what it takes operationally to make the strategy successful. In this episode: → Why service is Alarm Masters' biggest sales advantage → The playbook for turning service calls into major projects → Why the first dollar from a customer is the hardest to earn → Building enough service capacity to support growth → How sales and service teams work together to create opportunities → Using service history to uncover replacement projects → Why face-to-face prospecting still works in an AI-driven world → The operational mistakes that can derail this strategy Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E50
    July 8 · 15 min

    The Leadership Hires That Actually Scale a Service Business

    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 executive-level talent. They also cover hiring ahead of growth, budgeting for A-players, lessons from promoting internally, and the framework they use to build a leadership team that can scale. In this episode: When to make your first executive hire Why operations becomes the biggest bottleneck Hiring ahead of growth Budgeting for A-player talent Internal promotions vs. outside hires Building your leadership team in the right order Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E49
    July 1 · 13 min

    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 customer complaints, payment disputes, and difficult conversations without letting emotions get in the way. They discuss why the best operators separate business from personal feelings, how customer history should influence your decisions, and when it actually makes sense to fire a customer. They also share the internal standards they've built at Alarm Masters, from eliminating gossip about customers to owning mistakes without throwing employees under the bus. If your business depends on recurring revenue and long-term customer relationships, these principles can help you protect both your reputation and your bottom line. In this episode: → Why you should never take customer conflict personally → How to prepare before every difficult customer call → When to refund, compromise, or hold your ground → Why long-term customers deserve a different approach → The danger of gossip inside your company → How to own mistakes without blaming your team → Creating internal standards for handling conflict → Protecting recurring revenue through better customer relationships Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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  • S1 · E48
    June 26 · 17 min

    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 attract top-performing salespeople, drive better results, and help security companies scale. They discuss why most operators underpay their sales teams, the dangers of commission caps, how to structure base salary vs. variable compensation, and why trust and transparency are critical to retaining great reps. They also share lessons from building Alarm Masters' sales organization, including how they handle quotas, clawbacks, commission timing, and incentive structures that keep salespeople motivated without creating desperation. In this episode: → Why paying salespeople more can increase profitability → The ideal base salary vs. commission split → Why commission caps destroy motivation and growth → Common compensation mistakes security operators make → How to structure quotas, accelerators, and clawbacks → Why salespeople need a clear path to wealth → Creating compensation plans that scale with your business → The importance of transparency and predictable commission payouts Connect: Stephen Olmon — https://x.com/stephenolmon Collin Trimble — https://x.com/TXAlarmGuy Owned and Operated New Episodes Every Wednesday! Subscribe For More

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Showing 1–20 of 21 episodes