Client Stories
Pilot Capital was built with the high-earning executive, business owner, and founder in mind. We do our best work for families looking for a trusted real estate partner.
*These following are real case studies from actual Pilot Capital investors. Alternative photos have been used to protect client privacy.
01 / Business Owner
Brian — Pilot Capital Investor Since 2019
“They have a really disciplined strategy that provides an incredible amount of transparency. I really like that they’re fully vertically integrated and have a value approach. I’ve invested in 4 Pilot deals.” – Brian M.
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“I have zero interest in managing property, which is why discovering Pilot was a game-changer for me. They handle everything, from transactions to acquisitions and property management. This full integration means I don’t have to worry about a thing. When you invest with Pilot, you’re putting your trust in a team that controls the entire process, providing unmatched visibility and peace of mind.
One thing I appreciate about Pilot is their transparency. Jason is always forthright about his own investments, which reassures me about their strategy. Their offering memorandums are clear and detailed, making complex information easy to digest. They provide quarterly updates that are timely and comprehensive, holding themselves accountable to their projections and plans.
I’m more focused on smart, safe investments than on maximizing returns. Pilot’s disciplined, value-add approach aligns perfectly with my investment philosophy. They don’t rely on market timing but instead improve properties through thoughtful strategies. This method, combined with their transparency and ease of communication, makes Pilot stand out. Investing with them means I can trust the process and focus on what matters most to me.”
02 / Multi-Exit Tech Founder
Anonymous — Pilot Capital Investor Since 2008
“Particularly in tech, companies can have a change in the guard and go downhill. Or they could be disrupted: Amazon could come into your market and disrupt your higher business plan. But real estate feels safer—at least if you had a decent thesis. That’s why I’ve invest in 10 Pilot deals to date.” – Anonymous
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“Being a startup founder—I’ve got deep roots in the tech scene.
But that also means, my wealth is tied to tech and the fate of my businesses. And as a founder, most of my earnings would come from equity, rather than a salary.
I always invested more in tech because I felt like I understood the industry, like I had an edge. Plus, I wanted the growth tech stocks could provide.
But after going through a few market ups and downs, I started to realize I needed to diversify. I needed to add in something more stable and less volatile to counterbalance all my stock portfolio.
Particularly in tech, companies can have a change in the guard and go downhill. Or they could be disrupted: Amazon could come into your market and disrupt your higher business plan.
When I met Jason & Casey—I quickly realized that they had an edge in real estate.
They went way beyond the typical investing philosophy of “I think this is a good neighborhood. I’ll buy an apartment and see how it does in five years.” They have an inside knowledge of the industry. They’re able to see opportunities for growth that others couldn’t.
I decided against owning and managing his own properties due to the headaches involved. I’m not a handyman. I would probably get frustrated dealing with service providers. It wouldn’t work for me.
The overall investment portfolio appreciation—during a year where I wasn’t working at all—has done better than probably any job could pay me.
And from my experience, real estate feels safer than stocks— if you have a decent thesis.
The most important part for me when investing in private real estate is trust: Do you trust the people? Do you trust their judgment, their integrity and their experience?
I can say without a doubt I trust the experience, abilities and integrity of Pilot Capital.”
03 / Post-Exit Founder
Rick — Pilot Capital Investor Since 2008
“After selling off my company, I had a lump of cash I needed to invest. I was already convinced on real estate—But I didn’t have the time or desire to self-manage a big real estate property myself. Plus, you need a team and resources to do these types of deals…”
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“After selling off my company, I had a lump of cash I needed to invest.
I was already convinced on real estate—as I’ve never trusted the stock market. Real estate was always steadier and a little less risky to me. I can go out and see it with my eyes. The stock market always felt totally outside my control.
But I didn’t have the time or desire to self-manage a big real estate property myself. Plus, you need a team and resources to do these types of deals.
I knew Jason from brokerage deals—and I always liked that he was never selling you anything. He’s presenting things to you and he’s explaining things. But you never felt pressured—you always made up your own mind.
When he presented the first syndication deal to me, 16 years ago: I had normal fears like anyone does around investing, but my approach has always been 2-fold:
First— I spread things around in different investments to minimize my risk exposure. I don’t have an investment in any one thing that would change my lifestyle if it failed.
Second—since I invest in several different asset classes, at the top of my list is trustworthiness over return. I have total trust in Jason and Pilot Capital. They take a conservative and realistic approach to investing which suits my values.
They’re judicious about what they invest in and often participate in the investment alongside us. That’s rare, especially compared to many other financial advisors.
Jason and his team at Pilot Capital have been honest, knowledgeable and transparent in all of our dealings, which is why I’ve invested in 6 Pilot deals to date.
I will continue to invest with them in the future—because I trust them, their process and believe they truly care about protecting my investment.
Of course, I’ve gotten great returns, but most importantly, I’ve gained a trusted partner that gives me access to unique real estate opportunities.”
04 / Start-Up Founder
Adam — Pilot Capital Investor Since 2014
“Coming from the start-up world, I love trying new investments and learning: real estate investing seemed fun and I was curious. But—I was worried I didn’t know enough about it. I knew the dangers of just writing a check without having any idea what’s going on. ”
– Adam D
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“A lot of times, you hide that you have any money—because people are always pitching you investments. And it’s hard to know what to do: everyone looks professional, has a nice website, and claims good returns.
It makes you feel like you need to be defensive—almost protect yourself.
But my biggest motivator is always trying to plan for my family. That’s my number one priority: make sure that everybody’s provided for.
I decided to invest with Pilot because a good friend recommended it to me. But even then, I didn’t want to be the “dumb money” on a deal.
Coming from the start-up world, I love trying new investments and learning: real estate investing seemed fun and I was curious.
But—I was worried I didn’t know enough about it. I knew the dangers of just writing a check without having any idea what’s going on.
When I talked to Jason and Casey, I felt like they actually cared. I wasn’t just another name in a list, like with the “big financial advisors” who would call me just to sell.
After investing with Pilot for over 10 years, I can say that I trust them completely. They’re going to do their best to protect my money.
No one can tell you 100% if an investment will go up or down—that’s the nature of it. But with Pilot, you know they’re going to try hard and do a good job.
I’ve also met more and more investors and people with only good things to say about them—that boosts my trust in them even more.”
05 / Former Tech Exec and Real Estate Owner
Sara — Pilot Capital Investor Since 2019
“I was working 10-12 hours a day at Microsoft and then dealing with real estate stuff. I ended up getting a property manager. And even then I eventually just got to the point where I didn’t want to deal with property decisions.” – Sara
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“I spent over a decade at Microsoft, my workdays often exceeding 12 hours. Real estate was my side hustle, offering a sense of control outside the tech world. But managing properties was no walk in the park.
Calls about crises, like roof collapses or vacancies, came too often, especially when I was abroad. Even with a property manager, the stress remained. It didn’t matter if I was half-way across the country for a work-trip,, property issues were a constant distraction.
I realized active management was limiting my freedom rather than enhancing it.
So, I changed my approach. I sold all my properties and shifted to real estate syndications. Now, I invest passively. I’m no longer a landlord; I’m an investor who receives updates and checks on earnings. I focus on my passions—travel and growing my photography business.
This shift has brought the flexibility I sought, aligning perfectly with both my lifestyle and investment goals. My advice? Adapt before you’re forced to. Align your investments with your life’s needs. Today, my investments are smarter, requiring less of my time, and I am more content with my financial landscape.”
06 / Retired Company Executive
Alan — Pilot Capital Investor Since 2008
“When I ask them questions, they answer honestly. I’m not getting b*llshit, I’m getting an answer. I’m happily retired but have monthly income I can count on for spending. My real estate investing portfolio has been a huge part of that. I’ve invested with Jason and Casey in 10 deals.” – Alan D.
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“10 years ago, I was sitting in my kitchen, watching my grandkids play. I knew I wanted to retire early. Time is the one commodity that you cannot replace. I knew I could never get it back. And I didn’t want to work until I was 65 and miss all these good years.
I marked the specific day in my calendar where the number of years worked plus my age would mean I could retire early; it was my date with destiny.
But retiring also meant leaving the safety and security of a steady paycheck.
Up until that point, I was only doing the “square box” type of investments: mutual funds, stocks, my 401k.
I had tried doing some real estate investing myself: a land-purchasing adventure I went on with a friend. It seemed like a good idea at the time—but we ended up losing money on the deal and had to sell off the land for less than we bought it for.
That was my only bit of real estate experience, but it kind of made me realize, “Oh, maybe this real estate world is a little bigger than I imagined.”
Which led me to believe I should leave it to the professionals!
I had a good job and had some extra cash flow; I was looking for places to put it.
So when I met Jason and Casey, I realized they could give me access to this opportunity that the general public doesn’t have. It was a huge opportunity for me.
And they also had a very clear track record of success; over our conversations, I saw they were competent, both as brokers and as investors.
I’ve invested with them for over a decade, in 10 deals.
I can tell you I’ve not only had great results, but that you can trust what they say.
When I ask them questions, they answer honestly. I’m not getting b*llshit. I’m getting an answer. Which is really important.
I’ve met with other real estate syndicators that made me feel like they just wanted my money.
Jason and Casey might not always get everything right—but they have the best intentions every time.
I trust Pilot because they respect my money, they’re good stewards.
Now, I’m happily retired but have monthly income I can count on for spending. My real estate investing portfolio has been a huge part of that.
I think we all have it innately in us that we want to look after our families. I feel relaxed knowing that my family is taken care of.”
07 / Business Owner
Craig — Pilot Capital Investor Since 2022
“Pilot gives you that family feel: you know the principals are intimately involved in every project. They’re not removed from the day-to-day like some giant company: they’re hungry, focused, and want to grow. They’re not off in Switzerland, they’re taking care of your investment.” – Craig
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“I run a construction company, so I have firsthand knowledge of real estate. Everyday I’m working with investors and developers.
From my experience I’ve learned, be careful with the people that aren’t hungry anymore. When investors get too big, too removed, or there’s too much private equity—the principals are off skiing in Switzerland instead of making sure your dollars are safe.
But, with Pilot, it’s different.
Pilot gives you that family feel: you know the principals are intimately involved in every project. They’re not removed from the day-to-day like some giant company: they’re hungry, focused, and want to grow. They’re not off in Switzerland, they’re taking care of your investment.”
