Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Evan Weinberger, President, and CEO of Staying Ahead of the Game, located in Houston, TX, USA.

What's your business, and who are your customers?

I founded Staying Ahead of the Game LLC (SAOTG) in 2006. After growing SAOTG to be the largest academic coaching and tutoring company serving the Greater Houston Area, I co-founded a sister company in 2016 called Illuminos Academic Coaching & Tutoring LLC in Northern Virginia that services the Greater Washington DC Metro Area. Our services provide 360-degree academic support for students in 3rd grade through college. From traditional subject tutoring to help students master the concepts in their academic classes to standardized test prep to completing college applications, we have experts in all areas to meet students’ content-specific needs. We also take over the role of being the homework police, so parents can rest easier in this new world of education where an increasing amount of work and teacher communication happens online. Our flagship, research-driven, proprietary, and award-winning executive function curriculum and approach that we incorporate into our work with students is what differentiates us from other tutoring companies. Our program covers critical topics such as organization, time management, study skills, self-advocacy, problem-solving, and impression management. All of this, coupled with our ability to communicate with others in a student’s support circle (e.g., psychologists, psychiatrists, teachers, counselors) to help connect the dots for families, is why we call what we do academic coaching rather than just tutoring.

Our customers are wonderful families with children in public or private school(s) who place tremendous value on education. Some of our students are underperforming relative to their potential, either due to lacking the executive function skills to complete their work on time or carrying forward unfilled learning gaps in one or subjects from previous years. Others are spending too much time on schoolwork and need to become more efficient. Others wish to reduce the stress and chaos in the home around school-related things. Many of our students have mild to moderate learning differences, such as ADHD or other processing disorders, and they are looking for compensatory skills to help them perform to their capability despite them.

Tell us about yourself

I discovered a glaring gap in the academic support space while I was in college. There were countless resources for ambitious students lacking financial resources to get money to offset the growing cost of higher education. A growing number of academic support resources to help struggling students get the subject-specific help they need (e.g., tutors and tutoring centers) to navigate their demanding coursework. However, I did not see anyone working with students to strengthen the foundational life skills (i.e., executive functioning skills) they truly needed to perform to their potential. More specifically, I saw a growing number of capable students falling short of their potential performance because they lacked the systems and skills to juggle the demands of school and real life. Certainly, the ability to pay for the growing cost of education and mastering course material are both important. However, possessing effective and research-driven techniques for organization, time management, studying, and managing impressions are critical for achieving success and delivering on deadlines. Too many students were underperforming in classes in college because they had not mastered self-management systems before college.

I had the bold idea of founding a company to address core skills that lie at the foundation of any successful student. In 2006, I founded Staying Ahead of the Game LLC, an academic coaching and tutoring company with an emphasis on helping students develop and strengthen their executive functioning skills. Having little formal business education and experience, I printed business cards for free at I reached out to schedule meetings with heads of schools all over Houston. Somewhat to my surprise, many agreed to meet with me. I explained
my unique approach to helping students and received wonderful feedback. I developed a curriculum from countless hours of research, adapted the curriculum from my work with some initial student referrals, and began assembling a team of stellar academic coaches with backgrounds primarily in education and mental health. After 10 years of hard work, Staying Ahead of the Game LLC has become the largest academic coaching and tutoring organization serving the Greater Houston Area.

In an effort to amplify the tremendous impact that Staying Ahead of the Game LLC had for students all over the Greater Houston Area, as well as certain areas in other major Texas cities, I co-founded Illuminos Academic Coaching & Tutoring LLC in 2016 with a partner to prove I could bring the model to other major cities in the country successfully beginning with the DC Metro Area. Now, both companies are thriving, especially given the devastating impact of Covid on kids’ education over the past couple of years. With the new locations, as well as the introduction of tools to effectively offer virtual services, I can proudly say we have now helped thousands of students all around the country with a growing team of over 150 academic coaches and tutors. We even have several students outside the United States, including Hong Kong, Mexico, Canada, and Scotland. Seeing our students succeed is what motivates me on a daily basis.

What's your biggest accomplishment as a business owner?

While disrupting the academic support services space in one of the largest metropolitan cities in the country is impressive, I believe that co-founding Illuminos Academic Coaching & Tutoring LLC is my biggest accomplishment to date because it validates the fact that the award-winning and proprietary program I created back in 2006 (and continue to operate today) is replicable in other places. As such, it paves the way for tremendous growth possibilities in the coming years as I seek to bring our unique and research-driven support to more and more students around the country and, eventually, the rest of the world.

After seeing so many of our students (current and past) achieve greater success in their academics, gain admission into wonderful colleges, land dream jobs, and accomplish major feats impacting the world in such a positive way, it warms my heart to think about the true impact of amplifying our efforts to reach more students in more places. I also enjoy seeing our current and former students do wonderful things with their enhanced motivation, organization, time management, confidence, self-efficacy, perseverance, resilience, self-promotion, critical thinking, and social skills.

What's one of the hardest things that come with being a business owner?

My biggest professional challenge has been figuring out how to transition from working so much IN the business to working more ON the business. I recalled an adage that I reiterated over and over again in my head: “If you want something done right, you do it yourself!” Consequently, I built my business around me. I learned how to do everything from pitching and selling to invoicing and collections to curriculum and program development to marketing and human resources. I did all of that on top of being the largest direct contributor to company revenue for nearly a decade. That adage served me wrong, at least when it came to building and growing a thriving business. After my first few years in business, I learned about a program hosted at Houston Community College called the Goldman Sachs 10,000 Small Businesses Program. It was an initiative spearheaded by Goldman Sachs in partnership with Babson Business School with the goal of helping small business owners who founded businesses demonstrate strong initial viability to grow and ultimately create jobs and decrease unemployment in America. I was the youngest business owner among the 50+ entrepreneurs selected to participate that year in the program. The program had a variety of learning modules and met for hours every week over a period of months. One of the modules was about business valuation and exit strategies. I had little interest in this module initially, but it proved to be instrumental in adjusting my mindset moving forward. It made me think about how to increase the value of my company. I realized I needed to start reengineering the machine I had created to operate smoothly without me playing such a critical role in the day-to-day operations. I needed to shift my focus to the more macro facets of the company, like further developing the company vision, establishing new lines of revenue, creating new strategic partnerships, and driving the marketing efforts at a high level to continue feeding the machine I created.

Ultimately, transitioning from “being the business” to “being the leader of the business” has been my biggest professional challenge. Interestingly, I did not even realize it was my challenge until I took that module in the Goldman Sachs 10,000 Small Businesses Program about valuation and existing strategies. However, once I had the epiphany, making the transition over the years that followed proved to be my biggest professional challenge. Throughout the process, I learned that part of being a successful business owner is understanding one’s own limitations (e.g., time, knowledge, expertise). Conquering this challenge, onboarding subject matter experts, and learning how to lead and delegate effectively and inspirationally have led to some of the most substantial periods of growth for the company to date. And I’m not finished!

What are the top tips you'd give to anyone looking to start, run and grow a business today?

First, assess the viability of your idea. Not every idea represents a true opportunity worthy of pursuing. There are a lot of variables in the equation. To name a few, an entrepreneur needs to consider start-up costs, ongoing costs, length of time until profitability, exit plan, and more. It is also important to identify competition, analyze the market, project demand fluctuations, and predict potential obstacles to growth.

Second, check with your family. Starting a business is hard and time-consuming. There will be wins, losses, long days, and many sleepless nights. You will need support and understanding from your family to get through the tough times. It is important they are all on board.

Third, secure good mentors. No one has all the answers. No one is an expert at everything. Securing a small group of trust-worthy mentors knowledgeable in different areas (e.g., law, finance, business) will prove invaluable to any entrepreneur. You need a sounding board.

Where can people find you and your business?


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