Capstone Connectors with Derek Simkins

Capstone Connectors with Derek Simkins Connecting investors with opportunities and creating success through trust, teamwork, and innovation.

I'm an Air Force veteran, newly married, and thrilled to be a first-time dad soon! My passion is connecting people in the real estate world, helping borrowers and private lenders create win-win opportunities. I focus on building trust and fostering collaboration through every deal, ensuring strong relationships and successful outcomes. Outside of work, I’m preparing for the adventure of fatherhood and embracing this exciting new chapter in life!

09/28/2026

A lot of people think the goal is to do 25 deals overnight.

It’s not.

For me, I’d rather work with someone one property at a time, get them through that first couple-deal hump, and build the relationship from there.

We’ve got over $100M in our funds, so we have the capacity to fund good deals.

If you keep bringing us good deals that make sense, we’ll keep throwing money at them.

No bu****it. No need to rush into 25 houses tomorrow.

Just build, learn, scale…

And when you’re ready to ramp up, we’re here. 💰👊

09/25/2026

I thought I was the fu***ng god king of real estate.

Biggest mindset f**k-up I’ve ever made.

One deal humbled the hell out of me.

We lost about $200K on the ARV, and once you factor in the interest-only hard money payments, we were roughly $250K in the hole.

That'll get your attention real damn quick. 😂

Instead of pretending everything was fine, we had to restructure the debt, rethink the strategy, and find ways to generate cash flow.

We eventually recovered a big chunk of the loss through other deals and used the profits to pay people back.

The lesson?

You can know what you're doing and still get your ass kicked.

The market doesn't care how confident you are.

Now I look at deals differently:

What's the downside?

What's the backup exit?

How long can I carry it if things go sideways?

Because the goal isn't to find deals that only work when everything goes perfectly.

It's finding deals that can survive when s**t goes wrong. 👊

09/24/2026

Ground-up construction is something I get asked about a lot.

And honestly, you don’t need to have the whole damn plan figured out before you start asking questions.

If you’ve got a contractor, you’ve built before, or you’re just thinking, “Hey, maybe I want to build instead of buy,” there are ways to structure it.

The key is finding the right piece of land, having a solid scope and budget, and making sure the numbers actually work.

And no, you don’t necessarily need to build in your own backyard. 😂

Sometimes the opportunity is 30 minutes away. Sometimes it’s another state.

Don’t limit the deal before you even run the numbers.

09/23/2026

Real estate is a relationship game.
If you’ve got a deal you’re seriously thinking about locking up, send it over before you sign your life away. 😂
We can underwrite it, give you hard terms, and sometimes you can even use that term sheet to negotiate with the seller.
Just don’t send me every damn property you find on Zillow. 😂
Send me the ones where you’re thinking, “Holy s**t, this could actually be a home run.”
That’s when we get to work.

09/22/2026

Some people you meet in this business, you just know you need to keep around.

Mitch is one of those guys.

We’ve been friends for over a year now, and he’s sent a ton of good people my way.

But it’s bigger than referrals.

When you find someone who’s genuinely good people, sees the value in what you’re doing, and actually wants to see you win…

You hang onto that relationship.

Real estate is full of people trying to get something from you.

The good ones? They’re fu***ng rare.

Appreciate the people who bring good people into your world. 🤝

09/21/2026

I’ve learned the hard way that sometimes it’s worth paying someone else to deal with the bu****it.

I tried handling this stuff myself before.

Filing complaints, making calls, chasing people down… it was a pain in the fu***ng ass.

So if I’m paying for a service, I expect it to actually be done for me.

I’m not looking to babysit the process.

If something isn’t working, I’ll get to the bottom of it. And if they won’t make it right, we’ll talk about getting the damn money back.

That’s how I like doing business. Take care of people and make sure they actually get what they paid for.

09/17/2026

When the lead flow gets crazy, you can’t treat every lead like they’re your only lead.

I’ve only got so many hours in the day.

So I pay attention to the people who are serious.

You asked for docs? Send them.

Need info? Get it back to me.

You’re organized, responsive, and actually moving the deal forward?

Now we’re fu***ng talking.

I’d rather work with 10 serious people who get s**t done than 100 who just want to talk.

And the same goes for investing. Slow and deliberate is perfectly fine.

One property at a time. Build the foundation. Then ramp up when the systems are ready.

09/16/2026

I love watching s**t like this happen.

You start with a small group, bring a few investors and lenders together, start sharing what you know…

And next thing you know, there’s 300 people in the room.

That’s what networking should look like.

Not just collecting contacts. Actually building a community where people can learn, connect, and help each other win.

I’m always down to be part of something like that.

Relationships open doors. The right ones can change everything.

Address

Asheville, NC

Telephone

+18287670133

Website

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