Jake Gray

entrepreneur, lover of baseball, live music & backcountry trails

Tsundoku is a Japanese word. Its rough translation is "Jake buys more books than he could possibly read in one lifetime."Some people utter this word with judgment, some with empathy.Regardless, I am grateful that Japanese culture created a word that captures the virtue of my book collecting habit. My wife still rolls her eyes, but those books are ready and waiting when I need to read them, and I actually do read quite a few of them.Some day I will take an armload of books with me to Japan and say thank you in person.

Printable art image above purchased from Printable Wall Art (an awesome small business).

© Jacob T. Gray. All rights reserved.


Early Career
After working in corporate accounting and finance and "old economy" small businesses for 17 years, I co-founded three operating companies starting in 2007. One of those companies was a miserable mess. The worst four years of my life, no contest. One was a fun retail store on the San Antonio Riverwalk that broke even. And one included a successful sale to a larger company in the same industry. Before co-founding those companies, I served as a Vice President for a publicly-traded media company and as a CFO for a portfolio of small businesses owned by a family office. I also completed a Master of Business Administration (MBA) from the University of Texas at Austin. I've managed and/or analyzed hundreds of different business models.
Financial Analysis and Data Modeling
Using Microsoft Excel daily for the past 30+ years allowed me to build complex financial models for startups and streamline financial analyses for small businesses. I enjoy learning new Business Intelligence (BI) and No Code tools and am currently learning to code in Python, which is my first programming language (other than BASIC in the 1980s and Excel, VBA and DAX since then).
This work includes Power Query, Power Pivot, Power BI and other data tools for building parameter-driven data models to clean, shape and analyze large (and sometimes messy) data sets, build KPI dashboards and streamline internal processes for small and medium size businesses (SMBs).I started Data Make You Smile LLC (click logo at left) to deliver TIMELY DECISION DATA™ to SMB clients and help them get the most from their existing software systems, increase their cash flow and avoid or delay the cost and distraction of an enterprise resource planning (ERP) implementation. You can subscriber to the TIMELY DECISION DATA™ newsletter at https://news.jakegray.site/.
Teaching Entrepreneurship
It was an absolute blast teaching the Entrepreneurship capstone course as an adjunct professor at Trinity University in San Antonio, Texas from 2008 to 2023. I enjoyed introducing fellow entrepreneurs to students and engaging students with the question "How do we model this?" when evaluating a startup business challenge like customer acquisition, revenue growth or staffing needs and labor costs for their new startup.
I am continuing this work with the online education platform, Startup Helm LLC (click logo at left), to serve first-time entrepreneurs with education, coaching and curated, like-minded peer groups, free of the constraints of a traditional college curriculum.Building companies from scratch can bring hard lessons, sleepless nights, compromised personal wellness, strained relationships, personal financial stress and missed opportunities to climb the corporate career ladder. However, building companies from scratch also brings autonomy, variety, and a future that unfolds in front of you.
It's an opportunity to create value for customers, owners and communities by solving customers' problems. I would not trade that opportunity or any of those hard lessons for a "normal job" career path. I share my own experiences with students to help them as they launch their first startups or seek entrepreneurship through acquisition (ETA).
How Did I Get Here?
Here - as in South Texas?
I grew up in Albuquerque, New Mexico, a beautiful city and landscape of (now) more than 500,000 people that spills out of the foothills of the Sandia Mountains and across the Rio Grande River. I miss hiking and camping in the high deserts and mountains of the Four Corners states, and my heart will always be there.
My first job was sweeping floors for $0.35/hour in my dad’s woodworking shop when I was eight years old. I endured the cold of an Albuquerque construction site at 20 years old while on winter break during college, with my teeth chattering from the cold, and my dad asking with a wry smile, “Are you going to stay in school?” My dad taught me an appreciation for hard work, and he and my mom sacrificed greatly for my education, so there wasn’t a risk that I would drop out. But I recognized the wisdom he shared in that question and hurried to graduate the next year.I came to San Antonio, Texas for college at Trinity University, and except for a couple years in Houston in the mid-1990s, I have been in the San Antonio area since 1986. First job, deep friendships, met my wife here, family moved here from ABQ…and the rest is history.
Here - as in SMBs and startups?
I worked for two of the “Big Six” accounting/consulting firms, then as a Vice President for a publicly-traded media company in the 1990s. I enjoyed those experiences immensely. But I wrote my first business plan in 1986 as a high school senior project in collaboration with a family friend with a background in sales. The BASIC programming language was the extent of my computer science background, but our plan was to build a company to resell desktop computers to small businesses and individuals. (You chuckle at that idea now, but in 1986 the computer was not ubiquitous, and naysayers still quoted Thomas Watson, president of IBM, who said in 1943: "I think there is a world market for maybe five computers.")
I wanted to start and operate my own business since I was a kid sweeping floors for my dad. That 1986 business plan was my first taste of what such an adventure might be like. I never looked back after leaving my last corporate job in 1997.
What I'm Working On Now
More building from scratch, with an emphasis on companies, like Data Make You Smile and Startup Helm, that do not require OPM (other people's money), that are focused on niche customer needs and that put smiles on customers' faces. I am also actively searching for small businesses to acquire through Balance Ventures LLC (click logo at left), so if you or a friend have a small business for sale, let's talk.
Click the Contact button on the home page to send me a message.


Raised in New Mexico, seasoned in Texas. Married 20 years and raising two amazing daughters who make their dad proud. Longing to live at altitude again soon.If heaven does not include live music, baseball, endless mountain trails and dogs (big dogs, not those neurotic little fluffy breeds)...well...I'm just not sure what I'll do with that information.Click the Contact button on the home page to send me a message.


I look forward to meeting you, and if I can help you in some way, even better.You can send a message in the form below.If you're willing, please include in the message box something interesting about yourself that few people know about you (like the "tsundoku" habit I shared on the first page of this bio, for example).I'll get back to you shortly.
~ Jake

Thank you

That's so cool that you stopped by and sent a note. I'll get back with you soon.Thank you!~ Jake