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.

Entry & Exit - Inside the Security & Fire Industry is a business podcast hosted by Stephen Olmon and Collin Trimble, with 58 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Stephen Olmon and Collin Trimble hosts Entry & Exit - Inside the Security & Fire Industry, a business show with 58 episodes published.

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  Episode #58

  The BEST Lead Source for Security Companies

  Sep 9, 202615 minS1

  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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  Episode #58

  Why Every Growing Security Business Needs a Finance Leader

  Sep 2, 202615 minS1

  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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  Episode #57

  How AI Agents Are Changing the Way We Run Our Business

  Aug 26, 202618 minS1

  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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  Episode #56

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

  Aug 19, 202619 minS1

  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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  Episode #55

  Should You Buy or Build Your First Security Company?

  Aug 12, 20269 minS1

  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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