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. 11h ago ·  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

  2. 5d ago ·  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

  3. 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

  4. May 22 ·  Video

    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 become the bottleneck, how it limits growth, and what eventually breaks when every decision runs through one person. They share lessons from scaling Alarm Masters, empowering employees to make decisions, and building a company that can grow without the owner at the center of everything. Inside this episode: → Why founders become the bottleneck → The danger of tying the business to your identity → How owner dependency hurts growth and exits → Empowering employees to make decisions → What breaks when every relationship runs through the owner → Building a scalable company structure 🔗 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

    16 min

  5. May 20 ·  Video

    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 break down the first full year running Alarm Masters after the acquisition — including the wins, the mistakes, and the operational changes that completely transformed the company. They share how they scaled the business 60% in their first full year, why hiring cheap talent hurt growth, how international hiring became a major advantage, and the lessons they learned rebuilding sales systems, operations, and technology from the ground up. Inside this episode: → Why hiring the cheapest option backfires → Building an international team that scaled the business → The mistakes they made with their first sales hire → Transitioning from legacy software to Salesforce → Balancing founder involvement vs delegation → Breaking company sales records three times in one year → How they grew Alarm Masters 60% in their first full year 🔗 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

    16 min

  6. May 15

    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 the marketing channels driving real growth for security companies today — from Google reviews and local SEO to AI optimization, outbound prospecting, and commercial lead generation. They share what’s working inside Alarm Masters, including the SEO strategy that helped land one of the biggest projects in company history, how AI platforms are changing customer behavior, and the channels that completely failed for them. Inside this episode: → Traditional SEO vs AI search optimization → How Google reviews impact lead flow → Outbound systems for commercial leads → Marketing channels that failed → Why tracking and attribution matter 🔗 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

    20 min

  7. May 13

    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 months after acquiring Alarm Masters — from stolen equipment and blacklisted domains to learning every role inside the company. They share the real lessons from stepping into a service business as young operators: resisting the urge to change everything, surviving technology disasters, building trust with employees, and discovering what kind of company they actually wanted to build. From making collections calls and site visits to uncovering broken systems and redefining culture, this episode is a raw look at what happens after the deal closes — when the real work starts. Inside this episode: → Why they focused on being great employees before great owners → The brutal technology and email issues that hit immediately → Lessons on working capital, WIP projects, and key man risk → How they earned trust with technicians and staff → The discovery that shaped their sales-driven growth strategy → The coffee-drop tactic that became a scalable pipeline engine 🔗 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

  8. May 8

    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 like ChatGPT to fully deployed agents handling quoting, support, and operations. From custom GPTs for sales and tech support to an estimation agent that turns plans into full quotes in minutes, this episode shows how AI drives efficiency, better customer experience, and margin growth — without cutting headcount. Inside this episode: → Why AI is both overhyped and underused → The 3 levels of AI adoption → Real examples across sales, ops, and finance → How one AI tool reduced multi-day estimates to 5 minutes → Why focus beats trying to automate everything 🔗 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

    19 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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