Steady progress, not perfection, is the key to successful property ownership
Owning a multi-family property isn’t about having it all figured out from the start. It’s about showing up—week after week, unit after unit—with a willingness to learn, adapt, and lead.
Yet one of the biggest unspoken struggles for newer (and even seasoned) property owners is confidence.
- “Am I charging the right rent?”
- “Did I handle that maintenance issue properly?”
- “Am I too involved? Not involved enough?”
These questions aren’t signs that you’re failing. They’re signs that you care. And caring is the foundation of long-term success in this business.
Gus Grimstad has seen this dynamic play out time and time again. He knows that confidence doesn’t magically appear—it’s built, one small decision at a time. And you don’t need to be an expert to move forward. You just need the right mindset.
Here’s how to grow your confidence as a property owner—no matter what season you’re in.
1. Understand That Confidence Comes From Action
Reading articles (like this one), listening to podcasts, and talking with other landlords is all helpful. But real confidence comes when you do the thing:
- Post the listing
- Make the repair call
- Raise the rent
- Send the renewal notice
- Walk the unit after move-out
These are the reps. Each time you act, you gather data and experience—and your instincts sharpen.
As Gus Grimstad puts it:
“You don’t become confident before you take action. You become confident because you took action—even if it was messy.”
2. Build a Repeatable Framework
Confidence also comes from knowing what to do next. That’s where systems come in.
When you build a simple framework for recurring events—like maintenance requests, lease renewals, or new tenant screening—you reduce stress and decision fatigue.
Try setting up:
- A “vacancy checklist” for each turnover
- A tenant welcome template
- A repair tracking spreadsheet
- Monthly property check-in reminders
When your processes are repeatable, so is your confidence.
3. Practice Transparency With Tenants
A lot of owners lose confidence because they’re afraid of not having all the answers—especially when a tenant brings up an issue they weren’t expecting.
But here’s the truth: your tenants aren’t expecting you to be perfect. They just want communication and follow-through.
It’s okay to say:
- “Thanks for bringing this up—let me look into it and get back to you.”
- “I’m not sure yet, but I’ll have an answer for you by tomorrow.”
Being honest builds trust. And the more trust you build, the more confident you’ll feel leading your property.
4. Track Your Wins—Even the Small Ones
Confidence grows when you can see that what you’re doing is working.
Start a “Property Wins” journal and log simple successes each week:
- “Unit 3’s leaky sink fixed in 24 hours.”
- “Sent out all rent reminders on time.”
- “Tenant renewed without asking for a discount.”
- “Finally hired a snow removal company for the season.”
Even small victories build a sense of control and capability. And when the next challenge hits, you’ll look back and remember: You’ve done hard things before. You’ll do them again.
5. Learn From Setbacks—Without Beating Yourself Up
Things will go sideways. A unit will sit empty too long. A vendor will no-show. A miscommunication with a tenant will cost you.
But instead of thinking, “I’m bad at this,” try:
- “What system was missing here?”
- “What warning sign did I miss?”
- “What can I change so this doesn’t happen again?”
Gus Grimstad says:
“Every time something breaks down, you’ve got a choice. You can let it shake your confidence—or you can let it sharpen your process. That’s where the real growth happens.”
6. Define Your Version of Success
You don’t have to be the biggest investor in your market. You don’t have to scale to 50 units. You don’t have to be on YouTube breaking down cash-on-cash returns.
Success can be:
- Getting through a year without burnout
- Having rent consistently paid on time
- Creating safe, clean homes people are proud to live in
- Reducing your stress around maintenance
- Having more free time than last year
When you know what you’re aiming for, you stop comparing yourself to everyone else—and start feeling grounded in your own version of the game.
7. Stay Connected to Other Owners
Confidence is easier to build when you don’t feel isolated.
Consider joining:
- A local landlord association
- A Facebook group or online forum
- A real estate meetup
- A monthly Zoom call with fellow owners
These spaces aren’t just for technical advice—they’re for encouragement, perspective, and camaraderie.
Gus Grimstad points out that property management can be lonely if you let it:
“But the moment you hear someone else say, ‘Yeah, that happened to me too,’ your confidence doubles. You’re not behind—you’re just learning.”
8. Reflect Quarterly, Not Just Annually
Don’t wait until December to evaluate how things are going.
Each quarter, take 30 minutes to reflect on:
- What worked
- What didn’t
- What you learned
- What you’ll do differently next time
When you reflect frequently, you adjust more effectively—and your confidence becomes resilient, not reactive.
Final Thoughts: Confidence Is a Muscle
You don’t need to feel 100% ready to get started. You just need to begin.
The more you lean into action, the more equipped you become. The more you take ownership of your decisions, the more stable you feel. And the more you define success on your own terms, the more enjoyable this whole process becomes.
Take a cue from Gus Grimstad:
“No one hands you confidence in this business. You build it. Slowly. Steadily. One unit, one choice, one quiet win at a time.”
So show up. Start small. Stay consistent.
You’ve got everything you need to lead your property forward—with confidence that grows right alongside it.