Scaling from Solo to 5 Person Team: 5 Key Steps

Most founders can’t stop being the hero. They’re addicted to being needed — to being the person who holds everything together. The old-school business advice says: “Hustle harder.” “Be indispensable.” But here’s the truth: I built a profitable, scalable business by making myself replaceable. Here’s how to create a business that runs without you 👇 ⸻ 1. The A.E.D. Method This is the framework I use to remove myself from day-to-day chaos: • Automate anything repetitive • Eliminate anything that doesn’t actually move the needle • Delegate everything outside your zone of genius Every task that lands on your plate should pass through this filter. Your attention is the most valuable asset you own — treat it like gold. ⸻ 2. Document as You Go If you do it more than once, systemize it. Create quick docs or videos showing: • The exact steps • Helpful tips • Mistakes to avoid • Resources or templates used One well-documented process can save you hundreds of hours — for you and your team. ⸻ 3. Build Leverage Through People Most founders wait too long to hire, spend too little when they do, and skip building real systems. Here are the first 3 roles that changed everything for me: • Executive Assistant → instantly gives you 20+ hours back each week • Content Manager → keeps your brand growing while you sleep • Operations Manager → ensures everything runs smoothly when you’re not around Stop hiring for tasks. Start hiring for ownership. Great people + great systems = exponential freedom. ⸻ 4. Architect for Freedom Design your business to serve your life — not the other way around. Decide in advance: • When you work (time freedom) • Where you live (location freedom) • Who you serve (client freedom) • What you create (ownership freedom) Every “W” you give up chips away at your independence. ⸻ 5. Protect Your Deep Work Your best ideas and biggest breakthroughs won’t come from busywork. Block out your mornings for deep, focused creation. No notifications. No scrolling. No noise. That time is sacred — it’s where your real growth happens. ⸻ Freedom isn’t luck. It’s built. Automate. Eliminate. Delegate. Document. And design your business around the life you actually want. ⸻ Enjoyed this? ♻️ Share it with someone who’s still trapped in their business instead of building one.

The smartest business owners don’t do everything themselves. Let’s be honest, we’ve all fallen into that trap. You start your business, you’re passionate, you wear all the hats, marketer, accountant, customer service, delivery person, and it feels good. You’re busy. You’re productive. But at some point, that same habit becomes the reason your business stops growing. Because the truth is, you can’t scale what only depends on you. The smartest entrepreneurs figured this out early. They understood that real growth begins when you stop trying to do everything and start building systems and people that multiply your efforts. It’s not about working less. It’s about working smarter. When you delegate: ✅ You buy back your time to think strategically. ✅ You allow others to bring fresh ideas to the table. ✅ You build a machine that runs efficiently, even when you’re not around. And yes, this applies to realtors as well. Many realtors think they must handle every client call, manage every listing, create all their social media posts, and even chase every lead themselves. But imagine what happens when you hire a skilled virtual assistant, a proficient social media manager, or a knowledgeable transaction coordinator. Your energy shifts from “surviving” to scaling. Delegation doesn’t mean you’re lazy. It means you understand that your time is better spent on strategy, relationships, and closing bigger deals. You can’t build an empire if you’re too busy sweeping the floor. So, as you grow your business or your real estate career, ask yourself: “Am I trying to do it all, or am I building a team that helps me do more?” The smartest business owners build leverage, not burnout. #Businessgrowth #Entrepreneurship #Delegation #Realestate #Leadership #Productivity #Scaling #Teamwork

🌱 Controlled Growth Isn’t Playing Small — It’s Playing Smart. At Tailored Management Solutions, we’re proud to be a small business — but let’s be clear: small doesn’t mean incapable. Being small means we’re intentional. Our portfolio is designed to match our company’s capacity, ensuring every client receives the quality, care, and attention they deserve. We believe in controlled, sustainable growth — expanding only when it benefits everyone involved: our board, homeowners, vendors, and our team. As we secure new contracts, we’re fully equipped to grow our staff strategically to maintain the high standards that define us. And just as we’re selective with our clients, we’re equally selective with our team. We vet experienced industry professionals well in advance of hiring, avoiding shotgun decisions that compromise culture or quality. We keep a Rolodex of talented professionals in our back pocket — ready to join when the timing and opportunity align. At the helm, we have a Certified Master Community Association Manager with nearly 20 years in the industry, someone who’s learned the do’s — and the don’ts — of what makes communities thrive and partnerships last. That experience drives our commitment to doing things the right way, not the rushed way. Uncontrolled growth might look exciting from the outside, but it often leads to burnout, turnover, and diluted service. That’s not who we are. We’re building a company rooted in purpose, balance, and long-term success. Don’t sleep on small businesses that grow with strategy and intention. We’re not playing small — we’re playing smart. #SmallBusiness #SustainableGrowth #Leadership #PropertyManagement #StrategicPlanning #BusinessGrowth #QualityOverQuantity #SmartGrowth

7 of the best mistakes I've ever made 👇 I started my agency, Brand Good Time, with zero kids, zero clue, and so much confidence it should’ve been illegal. Here’s what I got wrong (and what it taught me): 1. I thought “testing and tinkering” was strategy. Learned that movement ≠ progress. Bold ideas are great, unless they’re just busywork in a cute outfit. 2. I joined a mastermind to “level up.” Learned I knew more than the person running it (humbling and infuriating). 3. I tried to grow my business through networking alone. Learned real momentum actually happens with relationship BUILDING. 4. I DIY’ed employee compliance. Learned the hard way that “winging it” is not an HR strategy. Hiring help for this was the move. 5. I DIY’ed my own books (😬). Learned that QuickBooks and I were never meant to be. Getting a real outsourced CFO team changed everything. 6. I believed every minute of childcare = productivity. Learned that rest is work, too. (Also: burnout is not a personality trait.) 7. I treated myself like my employees. Learned that “fair” doesn’t mean “equal.” I built the flexibility and freedom I have, and I deserve to use it. Now, I hire the right people (CFO, ops, contractors, dream team). We’re remote, flexible, fun, but with boundaries that keep us sane. At Brand Good Time, we embrace failure (literally tell my team two things: don’t be afraid to fall on your face a few times, but also please don’t make a $1,000 mistake lol). We either succeed, or we get a reaaaaally good story out of it.

I’ve seen a lot of business owners fall into the same trap, especially when they’ve just left employment: They take the employee mindset with them. You know the one… You set your first revenue goal based on what your next job title would’ve paid. It feels logical. Sensible. But it quietly keeps you stuck trading time for money, like you’re still clocking in – only now you’re the boss - and HR - and finance etc. Then as we grow, we do the same thing. We stick people on day rates, working out hours, still trading time for money. Then there’s the baggage we bring along for the ride. The harsh feedback that still stings. The culture that rewarded burnout and called it commitment. (Which also twists our perception into thinking it’s normal, so we expect it in others) To really grow, a few shifts have to happen – specifically: 1. From time-based pricing to value-based offers 2. From maxing hours to maximising impact 3. From playing it safe to tolerating the discomfort that comes with real growth It’s awkward at first. It was for me too. But that’s where getting ready to scale begins. So here’s what I’d love to know: What’s one “employee habit” or belief you caught yourself carrying into your business… and how did you finally drop it?

I’ve seen a lot of business owners fall into the same trap, especially when they’ve just left employment: They take the employee mindset with them. You know the one… You set your first revenue goal based on what your next job title would’ve paid. It feels logical. Sensible. But it quietly keeps you stuck trading time for money, like you’re still clocking in – only now you’re the boss - and HR - and finance etc. Then as we grow, we do the same thing. We stick people on day rates, working out hours, still trading time for money. Then there’s the baggage we bring along for the ride. The harsh feedback that still stings. The culture that rewarded burnout and called it commitment. (Which also twists our perception into thinking it’s normal, so we expect it in others) To really grow, a few shifts have to happen – specifically: 1. From time-based pricing to value-based offers 2. From maxing hours to maximising impact 3. From playing it safe to tolerating the discomfort that comes with real growth It’s awkward at first. It was for me too. But that’s where getting ready to scale begins. So here’s what I’d love to know: What’s one “employee habit” or belief you caught yourself carrying into your business… and how did you finally drop it?

You ever had one of those weeks where you're "working all day"... But when you look at your to-do list, nothing feels done? Same. That’s when it hit me. Maybe the problem isn’t that we don’t have enough time. Maybe it’s that we’re spending it like we’ll never run out. Even when you know you’ve got a bigger mission, you’re stuck updating spreadsheets, fixing slides, answering DMs, and checking if that invoice was sent. (Spoiler: it wasn’t.) Here’s the hard truth: You can’t make more time. But you can buy it back. Every business owner hits that point. You’re too busy keeping the machine alive to remember you built it to take you somewhere. And if you don’t fix that soon, you’ll start resenting the very thing you prayed for. So no, hiring isn’t a luxury. It’s leverage. Here’s what that looks like in real life: Stop doing tasks someone else could do 80 percent as well as you. Systemize anything you do more than twice. Outsource what drains your energy. Spend your best hours on what actually grows the business. Because you weren’t built to be the most efficient worker. You were built to be the most effective leader. Time isn’t the goal. Leverage is. And the moment you start buying your time back, you finally get to use it where it counts. That’s how your business stops owning you... and starts scaling without you.

Most founders I meet are stuck in the weeds of their own business. The company can't really run without the owner. I see this pattern over and over. Lloyd Thompson sees it too. Here are four reasons it happens: 1. The Unicorn Hire Fantasy You're waiting to hire someone who can do everything you do. That person doesn't exist. Instead, break down your role. What are the individual tasks? Hand them off piece by piece. Start with automation and admin. Then marketing and delivery. Sales and strategy come last. 2. Death by a Thousand Notifications Text, phone, WhatsApp, team chats, email, Zoom. You're responding to messages all day. Never getting to the work that actually moves the needle. The fix: Reduce your channels. Pick two or three. Set clear patterns for how you use them. Lloyd uses Slack for his team. Scheduled Zooms only. Email goes to support unless it's critical. 3. Vacation Dread You know if you disconnect, things will fall apart. So you take the laptop. Hunt for wifi. Check in constantly. I just spent one week in Fiji. Had three pre-arranged mentor calls. Could have done them from my phone. The next week I went four-wheel driving on K'gari Island. Barely any wifi. Left the laptop behind. Business ran fine both weeks. But most founders can't do that. Not because they have bad teams. Because the infrastructure for delegation doesn't exist yet. Here's the approach: Treat vacation as a testing ground. List everything that must happen while you're away. Assign owners. When you return, review what broke and why it needed you. Fix the problem. Then fix what caused the problem. 4. Delegated Work Keeps Slipping Tasks get missed. Deadlines slide. You think the answer is firing everyone and hiring A-players. But the real issue is infrastructure. You need visibility and verification. Accountability charts that map who owns what. Process ownership so someone is responsible for keeping systems updated. Regular check-ins to confirm things are getting done. Most founders skip straight to blaming the team. The environment wasn't set up for them to win. If you're stuck in any of these patterns, you're not alone.

How to Build a Business That Profits in Your Sleep If you’re still grinding 12-hour days just to keep your business afloat, let me share a truth: You don’t own a business; you own a job with overhead. Building a business that profits while you sleep isn’t about chasing “passive income.” It’s about creating a machine, systemized, scalable model that runs whether you’re in the office or on a beach. In my 30+ years leading businesses from startup to $100M+ exits, I’ve learned this: Success that sustains itself is never accidental. It’s engineered through the six core competencies I define in The CEO’s Playbook for Scale: ✅ Leadership & Vision – Build a culture that moves without you. Hire leaders, not helpers. Empower decision-making at every level. ✅ Financial Acumen – Know your numbers better than your bookkeeper. Cash flow, margins, and KPIs are the pulse of a healthy business. ✅ Sales & Marketing – Focus on recurring revenue streams: Subscriptions, retainers, memberships. These are the engines of sustainable income. ✅ Operational Excellence – Systematize everything. McDonald’s didn’t get rich selling burgers; they got rich by selling consistency. ✅ People Management – Build an accountable, self-healing culture that identifies and fixes problems before they reach your desk. ✅ Customer Service – Deliver a remarkable experience so strong that clients renew, refer, and advocate for you on autopilot. When I owned my trucking business, I thought long hours meant growth, until I replaced myself with leaders, built documented processes, and focused on automation. The company scaled to $6 million annually and continued growing while I was asleep. The formula is simple but not easy: → Systemize everything. → Delegate relentlessly. → Monitor metrics, not people. That’s how you build a business that prints profit, without draining your life.

I’ve worked with 100+ construction operators in the last decade.  Here are 3 mindset traps that keep most of them stuck: I’ve seen it up close.   10+ years in the industry.   Worked with small crews.   Scaled larger operations.   And the #1 thing holding folks back?   They chase steady over scalable.  Here’s why that’s dangerous:  1. “Steady” kills urgency.   → You stop selling because you’re ‘busy now’.   → Pipeline dries up while you're stuck on-site.   → Suddenly, you’re panicking for the next gig.  2. “Steady” handcuffs your time.   → Most small teams work in the business.   → All day on jobs. No time to grow.   → Zero thinking. Zero systems. Just survival.  3. “Steady” guarantees stagnation.   → You hire only when desperate.   → You never raise your rates.   → You stay small by default.  But here’s what scalable looks like instead:  1. You forecast demand.   ↳ You’re booked 3–6 months ahead.   → You say no to the wrong jobs.   → You build leverage, not just labor.  2. You create a surplus of leads.   ↳ Systems bring clients to you.   → Online presence works while you sleep.   → You’re no longer chasing — you’re choosing.  3. You build a business, not a job.   ↳ You replace yourself in operations.   → Estimators quote. PMs manage.   → Work gets done without just you.  “Steady” gives you lunch today.   “Scalable” gives you freedom tomorrow.  When you're proud of being ‘booked solid’...   Ask yourself: are you just busy — or are you building leverage?  Freedom doesn’t come from full schedules.   It comes from predictable, multiplied opportunities.  "Proudly stuck is still stuck."  P.S. Are you chasing busy work or building true freedom?