Re-Engaging Alumni Entrepreneurs


‘Steve’ is a major gifts officer at one of the country’s most prestigious universities. This school is also a vibrant entrepreneurship hub, piping startup founders into the economy at a furious clip. But Steve’s facing an all-too-common issue. 

In fact, I connect with 2–3 fellow Higher Ed professionals each month around these themes, and I ask each of them to share a story, a challenge, or an idea to jumpstart our conversation. This is by far what I hear most. 

Steve’s having trouble engaging an alumni entrepreneur. The alum is youngish, and is CEO of a startup company he founded. The company is profitable and has grown to about a hundred employees. He is an occasional annual fund donor who loves his alma mater. He’s responded to Steve's outreach — but warily. 

“I’ve met with a couple of you guys before. Are you just coming to ask me for money?”

There is a LOT going on in these two sentences. Let’s break it down. 

First off, this is tough. The positive zing of hearing from an alum is offset by the signal that he’s unhappy. But I’ll take a negative response over silence any time. At least you have something to work with as you repair this connection.

And repair it you must! This is an alum who has gone from early stage founder with zero capacity to CEO of a profitable 100-person private company. The university and his peers now see him as a potential leader and investor who can help move the school forward. If Steve can’t re-engage him, the distance will only grow.

“I’ve met with a couple of you guys before.” From this, we know he was more open to meeting in the past. What changed? He probably met with a first gift officer and they didn’t quite hit it off. Perhaps he considered it an anomaly, and he took the meeting with the second gift officer. When that meeting didn’t feel like time well spent, either, it became a pattern. Now he needs to gut-check every visit.

These are good fundraisers — some of the best in the business. But I’ll bet they approached this alum as they would any other supporter. Startup founders’ needs and engagement patterns differ significantly from traditional philanthropists. Fundraisers need to be equipped to relate specifically to alumni entrepreneurs. 

Given the high turnover in our field, basic ‘entrepreneurial relations’ skills are especially critical for Advancement offices. If these relationships with entrepreneurs must be sustained through multiple gift officers, gaps in engagement may result in depressed involvement and giving among successful founders.

“Are you just coming to ask me for money?” As fundraisers, we understand the philanthropic process is most effective when it’s authentic — when we acknowledge that philanthropy is the goal, but that the value of that generosity truly goes both ways. 

The alum’s dismissive statement tells us that he hasn’t experienced this authenticity in his relationship with his alma mater. 

It also tells us that he wants more than ‘just asking for money’ — he actually desires an authentic connection with the school. It means enough to him that he’s willing to respond to Steve, but the interaction to date hurts him enough to express his dissatisfaction somewhat brusquely. 

Every situation is different, but when you encounter this, try responding with this three-step plan. 

Acknowledge the distance.

Face this issue head on. Be gracious in suggesting that the burden of this lies with the university, and that perhaps the institution hasn’t helped the alum to stay as connected as he’d like. Say that you’d like to remedy this, or at the very least understand its roots, so that future alumni entrepreneurs can stay meaningfully engaged. 

Offer value.

Signal to the alum that this interaction will be different by showing that you understand his needs. Demonstrate that you’ve done your homework, and acknowledge the alum’s accomplishments, company milestones, or recent news. Then, combine what you’ve learned with the Rule of 4 (Recruiting, Networking, Visibility, Special Experiences) to offer something that might interest your alum.

Is there a resource that might be helpful to him or her — a resume book, company news you could share on social media, a particular intro that might be relevant and helpful? This could lay the foundation for a productive and authentic relationship with your alumni entrepreneur. 

Be specific with your request or engagement opportunity.

Now that you’ve sent key signals that you're listening and doing things differently, go ahead and make an ask. Make your message succinct. Your ask might be as simple as a 20-minute call to recalibrate the relationship. Or, you might need to tap him as a student mentor, or invite him an upcoming event. 

In those cases, try to tie the engagement opportunity to a benefit that he might experience for participating. Frame that benefit in the context of the Rule of 4. Will it help expose the company to talented undergrads? Are there other alumni attending the event to whom you could connect the alum? 

You may need to make a financial ask. Not the ideal next step here, but we must find a way to ask when the need arises. In this case, think about whether your ask aligns with the entrepreneur’s likely financial situation. Startup employees, even those at fast-growing, buzzworthy companies often trade current income for equity. Explore this gently with your alum, after doing what you can to understand his or her unique situation. 

Good luck. And keep me posted!

Steve handled this situation deftly. I’ll plan to check in with him soon to see how things went. 

Have you overcome this issue with an alum? How have you approached it, and what has or hasn’t worked for you?