Prospecting Donald Trump

Back in 2004, I held the role of Senior Account Manager for an Educational Technology SaaS company covering the Northeast. That's when I first heard about Trump University. At the time, educational technology was still in its early stages, and I envisioned a collaboration with Donald Trump to build a cutting-edge company that would not only help me achieve President's Club status, but also establish a prestigious higher education institution known worldwide. After all, I was a former Educational Psychologist and Trump had expressed to reporters that he hoped to create a “legacy as an educator” by “imparting lots of knowledge” through his program.

As an ambitious sales professional, I embarked on a mission to prospect "The Donald" and secure a meeting with him and his team to pitch my idea. After delving into books like "The Art of the Deal" and "Think Like a Billionaire" to gain insights into Trump's mindset and characteristics, I crafted a strategy on how to approach him. I also immersed myself in researching Trump University and its objectives.

As way of background, Trump University was founded in 2004 by Donald Trump, and his associates Michael Sexton and Jonathan Spitalny. The company offered courses in real estate, asset management, entrepreneurship, and wealth creation until 2010. Despite its name, the organization was not an accredited university or college although that was not clear to me when I was prospecting them.   

Upon discovering that Trump didn't use a computer and his secretary opened his mail, I penned a letter outlining a compelling solution for Trump's venture and framed it in a black frame and had it express-delivered to capture his attention. The letter included a logo that I created, "Trump University, powered by Plato," and in that letter I proposed helping him to tap into the fastest growing higher education market segment that he was missing and outlined how we could work together to benefit from this revenue stream. I highlighted how our software improves student achievement and was available 24/7 without the need for instructors. As a hook, I did not, however, share with him what the fastest growing higher education sector was in order to pique his curiosity and get an initial meeting.

What I knew as part of my work as an Sr. Account Manager in higher education was that the developmental education sector was growing so rapidly that most higher education academic institutions were struggling to keep up retention rates and respectable outcomes. They were burdened by the need for incoming students to play academic catch-up before they could take credit-bearing courses.

I hoped that Trump would want to take advantage of our ability to remediate students online and support them remotely using our software. At the time, this was the emerging model employed by hundreds of institutions across the country to aid in remediation, retention, and student outcomes.

Days later a phone call came through while sitting in my home office. “Hello Mr. Ahern, this is Michael Sexton, President of Trump University”. Before the caller could say anything further, I interjected, “Cut the crap, Brian. Don’t bust my ass", and I hung up.  I thought it was my old friend Brian Clifford, who I had briefed previously about my audacious goal to collaborate with Donald Trump. A minute later, the phone rang again and to my disbelief the caller said. “Mr. Ahern, this is Michael Sexton with Trump University, we would like you to meet with us in NYC”. Suddenly, I realized my mistake, and immediately regrouped and within minutes had an appointment in NYC to meet the Trump University team.

As I entered the building in lower Manhattan, I was greeted by Michael Sexton, President of Trump University. He was cordial and polite and took me on a tour of the facility. I was impressed with the number of coders’ hard at work, with what I assumed to be creating content for delivery for this online university.

Before long I was escorted into a large conference room. After outlining my online software capabilities and the issues impacting higher education retention, student achievement and challenges with online learning, I pitched the idea of Trump University powered by Plato concept. I thought it went well and returned home high as a kite.

A few days after my return to my home office in Connecticut, I received a call from Trump University informing me that although the team liked the program and the proposed partnership, they decided not to proceed with our partnership. Their focus was on highly prepared young adults aiming for success in specific courses like Entrepreneurship, Real Estate, and Marketing, not the broader student population I had envisioned and failed to qualify.

While I never met Donald Trump, I did achieve President's Club status, and in hindsight, considering the fate of Trump University, it may have been a blessing in disguise.

Over the years, I have shared this experience with numerous sales professionals as a lesson in prospecting and learning from setbacks:

1. Instead of letting fear get the best of us, take the risk. Don’t look at how big the prospect is, look at how big your goals are.
2. It's only when we stop fearing failure that we can fully seize an opportunity.
3. Great dreams require great faith and courage. If you aren’t failing and making mistakes your goals and dreams aren’t big enough.
4. Qualify the opportunity with thoughtful open-ended questions before committing time and resources.
5. Commit to thorough research and ensure your value proposition is aligned to the prospects vision and goals.
6. Always answer the phone with professionalism.

I hope this mini case study on prospecting serves as inspiration and provides valuable insights on engaging with elite prospects and entrepreneurs, emphasizing that with the right mindset, our possibilities are endless.