April 13, 2024

Investor Feature - Real Estate - Craig Wear

“I’m really excited about having passive income show up in the checking account, knowing that experts are making decisions, and I don’t have to micromanage every part of my financial life.” 


Navigating Life’s Highways 

After touring the country for seven years by motor coach, Craig Wear and his wife of 41 years have finally re-entered the “stick and brick world” and settled close to their sons in the Denver area. “I had a fee-based financial planning business for 32 years. When I sold it seven years ago, our kids were all gone doing their thing and we thought, ‘If we’re going to live the adventure, let’s go do it now.’ So, we sold almost everything we owned, bought the big bus, and off we went,” says Craig of their incredible journey.  

Despite offloading the business, Craig has kept himself busy with family, the great outdoors, and a new business venture. “We love to hike, flyfish, and ride motorcycles across the country; and we developed really neat relationships from the time we spent in the RV world,” he explains.

“Somewhere in those seven years, I started another business that is a pure financial consulting business focusing very specifically on solving tax issues for people who have large IRAs. That company has just taken off and done phenomenal things.” 

For Craig, one of the perks of assisting others with their finances is a more informed view of his own goals and strategies. At this new juncture, Craig reports, “the objectives we have are really tax-advantaged cash flow and appreciation over time. I still have my business and plan on being active in it for several years. That gives us time for a lot of these passive investments to really do their job––to shelter some income from my business in the short term and to provide us with a stable income once we transition.” 


On the Road to Real Estate Success 

Finance-savvy Craig views real estate investment as a family tradition. “My early investing experience was really as a teenager watching my father buy rent houses,” Craig recalls. “He did very well and ended up with 15 single family homes in the subdivision where we lived.” 

In addition to learning about cash flow and appreciation, Craig says, “the other part I learned was through personal experience. Dad worked all the time, so even at thirteen-years-old when somebody would move out of the house, it would be Craig on his banana-seat bicycle pulling an edger and mower with a broom and some plastic bags to go clean up. It was pretty formative for me; I learned how to paint and fix fences and all sorts of things.” 

After learning the fundamentals of investing through his college degree in finance, Craig entered the financial planning industry in the mid-1980s. “That’s when the real education started,” he says. “Not only in traditional stock and bonds, but there are a lot of wholesalers who spend their lives representing big retail, real estate syndications, calling financial advisors to convince them to sell those products to their clients. Many of those programs didn’t have a lot of economic benefit to them. You didn’t really care what happened to the money because you were getting a 70-, 80-, 90-percent tax deduction on the front end.” 


Planning the Next Investment Milestone 

Thirty years of experience in the field of finance convinced Craig that, “Investing only for tax benefits has its drawbacks. I learned that real estate did have some great returns, but I also learned that the typical available real estate syndications that come through the brokerage world and the securities world have so many layers of fees and so many people putting their hand in the investor’s pocket that by the time investors get to the deal, they don’t get the best returns.” 

Following his own instincts, Craig took a different approach––one that’s familiar to many real estate investors. “My wife and I bought single family homes; we managed them, we flipped them, and they did well by us, but they were also a lot of work,” Craig admits.

“I had clients that developed large real estate portfolios: single family portfolios of up to 90 houses and apartment complexes. I saw the benefits they were getting out of it. I also saw that it was a business for them. And it was lucrative, but it was a lot of work. I got to see their rates of return, cash flow, and everything else.”  

When it came time for Craig to make decisions for the next phase of life, these insights inspired him to research private syndicators that work directly with investors.  



Fueling the Future with Ashcroft Capital 

According to Craig, many of the options he found reminded him of the past. “A lot of them structure their deals where the benefit is mainly to them, or they don’t have a lot of experience. They have a great story and a good sales pitch, but they don’t have the real proof.”   

Then, Craig found Ashcroft. “One of the companies I got excited about was Ashcroft. I wanted passive because we’d done active, and we were at a place in our life where I’ve got more important things to do with my time than mowing a yard or hiring and firing a manager to run an apartment complex for me.”  

When Craig spoke to the Ashcroft team and learned more about the business, he says, “I was blown away by their performance history––the number of full terms they’ve done and the kinds of returns they’ve generated. What I really liked about them compared to a lot of the other syndicators is that all their management is in-house, so they control the whole process and have their own construction team. To me, that means lower costs to do the work and higher quality control.”  

“The confidence that I have in setting up the next chapter of our life is really enormous when I consider what Ashcroft is and what they’ve done in the past. I feel confident in the projections that I have for what’s going to happen for my wife and me.” 

Given that Craig has converted much of his savings to Roth IRAs, he also appreciates the tax advantages he’s able to enjoy through Ashcroft investments. “They’re allowing me to take full advantage of the tax code to offset other income that we have through some passive income that I get from my business,” states Craig. “A really big part of our future retirement plan is based on the income streams and returns from Ashcroft, as well as a few others.”  


Shifting Gears from Financial Worry to Financial Freedom 

Although Craig’s fruitful investment strategy is the culmination of decades of life experience and career success, he believes he is “one of the most fortunate men in the country for a lot of reasons.” Above all, he gives credit to his family. “I found a woman who’s very patient and just a fantastic wife and an equal partner to walk through life with, and she enables me to do all kinds of great things,” brags Craig.  

“Secondly, my career has afforded me an uncommon view into the lives of thousands of people who were always 15-20 years ahead of me,” he explains. “Somehow, I learned to listen and pay attention to what they did right and what they did wrong. The ones that really succeeded and had freedom from a lot of worry and anxiety were the people who put money in non-traditional or alternative places. So, I’m just trying to emulate a lot of what they did.” 

The most important lesson Craig would pass on to would-be investors is that investing in real estate is like starting a business. “And they’re going to learn some things, just like any business,” he says. “I’m choosing to let the pros manage that section of my financial portfolio. I want their team (who has a tremendous amount of experience in acquisitions) to make the management decisions, deal with the financing, and ultimately decide when the best time is to get rid of a property.” 

“Real estate is a business, you’re going to put a lot of money into it. You’re going to make mistakes if you go do it yourself, whereas syndicators have already made their mistakes years ago. Now, they’re presenting the best options available through the experience and wisdom they have.” 

Without financial worry keeping him awake at night, Craig can focus on what matters most to him. “I’m really excited about having the option to work until I don’t want to, and to be at a place in my life where I’m able to make significant additions to our investment portfolio.” And the ultimate payoff? “Ten acres looking up at the Rocky Mountains, in a house that my wife chooses, with a shop for me to work on my motorcycles and build furniture. I don’t know if it’s going to get any better than that.”  

Craig is just one of our 3,000+ investors. Hear what passive income has meant to over 100 of our investors.