June 6, 2023


“I’m trying to get to the level of Job-Optional.” 

Jennifer Skeen knows a lot about hard work. She worked multiple jobs for most of her life, paid her own college tuition, and even saved enough to buy her first townhouse after graduation. 

A molecular genetics and biochemistry expert by training, Jen is now an executive leader in biotechnology and a single mother of two daughters.  

If the job description sounds exhausting, that’s because it is. For Jen, the demands of her role and the unpredictability of her industry led her down the path to real estate investment in hope of designing a less stressful future. “It’s always nice to have a second stream of income. Biotech is pretty volatile. Even the bigger companies restructure frequently, so jobs are never secure. Being in a higher-paid category, it’s a huge hit when you lose your income. Knowing if that happens I have a little bit coming in to bridge the gap gives me a safety blanket.”  

The Science of Building Passive Income 

Jen started investing seven years ago after her divorce, which she calls a difficult financial lesson. But she quickly dove in with scientific rigor, learning about FIRE (financial independence and retiring early) and the investment types that could help her reach her goals.  

At an Ashcroft event in San Diego, where Jen lives and works, she met investors who had been through a full turn and noticed, “They were all really happy.” And that’s not all that gave her comfort: “Being new to this investment space, it can be a little nerve-wracking that you’re making the wrong call. But the Ashcroft name is really well respected, the people are public––talking at conferences; they have their own podcast. They’re not going to disappear and take your money. There’s a level of security and comfort that they have your best interest in mind. We’re all in it together to make a little money if we can, in an ethical way.”  

Jen had joined a publicly traded company at that time, and the compensation package inspired her to find ways to not just save but invest her money. Like many new investors, Jen started out with single family rental homes, purchasing four new-construction properties in Ft. Worth, and an additional two in Florida. However, she soon discovered the stresses of remote property management and decided to sell the homes in Texas.  

“Passive! I want to be passive. I’m 46 and I want to retire in about four years with a comfortable living.”  

Jen made the decision to roll the proceeds into a deal with Ashcroft. “It was a hassle for an out-of-state investor, and the market was popping, so I decided I would just cash in. Instead of flipping them into a 1031 exchange so I would reduce my taxes, I decided to put the money toward a passive investment with Ashcroft, where I could take advantage of accelerated depreciation to help with taxes. Ashcroft is a really reputable company and well-known in the investment community, so I felt really comfortable.”  

Detailing her thinking, Jen explains, “I split apart two bonuses, and I wanted to put it somewhere I wouldn’t touch it for a while so I could grow it. I put $25k into Eagle Crest and $25k in the Vista properties.” Jen also recently added to her previous investments in the Value Add Funds II and III. “It’s not just one property, so I like the diversification of multiple properties there. And they also have this new waterfall based on how much you put in, plus a new 10% kicker on monthly distributions.”  

“It’s nice to see that they’re actively working to maintain and create additional value for investors. I have a ton of trust in the group.” 

Hard work pays  

All of Jen’s efforts are building toward a carefully engineered plan for a well-deserved early retirement. Regarding her recent investments, Jen says she’s, “using them in preparation for cashflow. When my kids are out of high school and I hit 51 or 52, I’m going to sell everything and travel the world! And I use the current funds I receive to pay down mortgages on my rental properties. That way, that additional cash flow will hit in about five years.” 

Investing isn’t the only thing Jen has down to a science. She has developed a useful ‘life hack’ that brings her financial, work, social, and personal life together in one view. “I have a ‘Master Control’ spreadsheet with dozens of tabs that I review monthly with net worth, account balances, spending by category, travel rewards points, upcoming vacation planning, rental property performance, retirement planning, doctor contacts for the family, and a bucket travel list of over a 100 places and activities that I want to accomplish. A guiding principle in my personal [sic] and professional life is to have one central source of truth and where I can find critical information.”  

It’s no surprise that Jen has found herself setting strategy and guiding teams, but she’s ready for a change of pace. “I’ve always been in a leadership role, so I have corporate responsibility and team responsibility. I’m always high-level analytical, and it doesn’t shut down when you go on vacation, so I’m really looking forward to being able to switch off that level of responsibility and do things I want to do. My goal is to take a two-year travel sabbatical and figure out what the next chapter is. I’ll have the time to figure out what I want to do next instead of what I have to do next.” 

Ever the methodical scientist, Jen has created a chart of over 200 travel destinations she hopes to explore. In retirement, Jen would also like to help other single women explore the world of investment. “None of us got the education––we don’t even know where to start. We don’t know the language because the lexicon is so specific: what is compound interest, arbitrage, tax deferrals.”  

With Jennifer Skeen on the case, we have no doubt the next generation of female investors are in good hands.  


Photographed below, Jennifer Skeen and daughters Kendall and Autumn Skeen