Major Gift Lessons From TV’s ‘Shark Tank’

I could just say (1) prepare, (2) prepare, (3) prepare, (4) prepare, (5) prepare and (6) prepare.

Did I mention that you really need to prepare? Essentially, this is the meta-message Kevin O’Leary, “Mr. Wonderful” on TV’s “Shark Tank,” tells would-be entrepreneurs seeking to get spots—and funding—on the show.

In “How to Present the Perfect Pitch: From the Shark Tank to the Boardroom,” O’Leary offers 10 tips on how to ace a fundraising pitch. Whether you’re seeking venture capital or a philanthropic gift, many of the principles are the same. I’ve selected six of O’Leary’s tips I find perfectly aligned with what it takes to make a successful nonprofit ask. Take them to heart, and you’re sure to make your next in-person fundraising presentation a winner.

Oh, and there’s one more important thing. Says O’Leary: “The No. 1 rule is to make your pitch incredibly dynamic.”

Let’s do it.

1. Keep it Simple

People are busy and have limited attention spans. O’Leary suggests making sure you can explain your business to an 8-year-old. It helps to think of your fundraising pitch the same way. If it takes more than a couple sentences to explain the opportunity you’re presenting, you need to go back to the drawing board.

Tip: Practice making your key points using plain language. I used to practice my asks on my son until I could get him to understand them. Practice on your own kid, someone else’s kid or, at least, someone who doesn’t work where you work. Another way to stay simple is to use the Flesch-Kincaid readability tests when crafting your solicitation. They keep language at a seventh-grade level.

2. Keep it Lively

Reframe your ask into a story, and use great storytelling 
techniques. Human beings are wired to listen to stories, and will pay greater attention than they will to a dry, fact-filled narrative. Make it compelling. There are two protagonists: your beneficiary and your donor. The beneficiary encounters all sorts of trials and travails. Paint that person as vividly as you can. Then make the donor the hero who helps the beneficiary overcome the troubles.

Tip: Get in touch with why you’re asking and engage your own passion. Authentically share your passion. Don’t make asking just a chore. Make it about crafting a captivating story. Once upon a time (introduce the current situation/problem) there was a young girl who lived (introduce the potential beneficiary). She faced many challenges (outline the emotionally charged issues) until one day (introduce your solution, and how the donor can help create a more positive outcome). And never forget that the best way to get someone to listen is to be 
passionate. Passion truly is contagious.

3. Bring Key Player(s)

There are two types of key players when it comes to making a fundraising ask: The first is the person the prospect will have the hardest time saying “no” to, and the second is the person with whom the donor has the best relationship. The “hard to say ‘no’ to” person is someone the donor perceives as important, authoritative, credible and friendly. The donor wants to talk to the “big cheese”—the person he or she perceives as responsible for assuring the gift does what it is intended to do.

The “best relationship” person may be the executive director, the board president, a doctor who performed life-saving surgery or a former teacher. If the director of development or a major-gifts officer built the relationship, then you may want that person to be in the room. You always want to have someone there who you know the donor will like—someone the donor already knows, or someone who is just genuinely friendly. Being likable goes a long way.

Tip: Be thoughtful about who should be in the room 
during the solicitation. Sometimes the “hard to say ‘no’ to” and the “best relationship” people are the same individual; sometimes they are not. If you need to bring two people with you, do so. Just don’t bring so many folks that you totally outnumber your donor and make him or her feel uncomfortable.

Tip: Decide in advance who will make the ask! If both of you think the other is handling the 
actual solicitation, you risk leaving the room without an answer. I’ve had this happen—where no one wants to step on anyone else’s toes. This is a waste of everyone’s time, plus it confuses the heck out of your prospective major donor. In one situation where we’d 
intended to ask for $200,000 (but didn’t), the donor sent us $5,000 immediately after the meeting. He was fed up with us, and wasn’t going to offer us a second chance.

4. Put All Numbers on the Table

Transparency is important. This doesn’t mean you have to weigh your donor down with statistics and pie charts. It does mean you have to have answers to any questions he or she may ask about the details of your proposal. Major donors want to know their gifts are critical to your success. They also want to know their investments won’t be going down a black hole. Your ability 
to answer their questions reassures them that they’re making a 
smart investment.

Tip: Craft answers to key questions in advance. How much will the total project cost? How many will it help? Specifically, how will the donor’s gift be allocated? Who will be responsible for the 
project’s outcomes? What will happen if you don’t raise enough? How do you know this will be successful?

5. Do Your Own PR

Don’t do a cold ask. Prepare your donor in advance if you want to get him or her engaged. O’Leary suggests to “Shark Tank” contestants that they won’t get much notice just 
because they’re selected to be on the program. He advises folks to be prepared to launch their own media blitzes and to become social media savvy.

By the same token, your major-gift proposal won’t get much notice if it’s the first time your prospect has ever heard of you or your project. Make sure you leverage your in-person ask with preparatory cultivation that puts your prospect in a positive frame of mind.

Tip: It’s the engagement, stupid. I’m sorry to use such a loaded word, but it really is dumb to think you can ask for a major gift without first engaging your prospect—multiple times and in multiple ways. You know, all the good stuff: events, tours, group get-togethers, one-to-one visits, phone calls, check-in emails, greetings, newsletter articles, social media, impact reports and lots of thank-you’s. It’s what you’d do in building a relationship with anyone else—a potential friend, a co-worker, even a family member.

Ultimately, you’re going to be asking for a huge favor. People don’t do favors for nothing. They give back to those 
who give to them! It’s called reciprocity—it’s a huge deal, and don’t you forget it! 
Create a reciprocity plan—a year-long individual engagement agenda with 
multiple interactions. Make sure they’re fun. Here are some examples:

• Become part of the family. Involve kids, grandkids, spouses, adult children and any other family members.
• Offer relevant volunteer opportunities so the prospect sees the mission come to life (tailor them to the different family members’ interests and talents—think of this as planting seeds that will grow and blossom, ideally over multiple generations).
• Offer opportunities for donors to get to know multiple folks within your organization. This deepens their 
engagement with you, and makes it richer. And it helps when there is staff turnover; if your donor has multiple connections with you, losing one won’t be the kiss of death.
• Ask folks to join committees. It’s terrific for networking and socialization (connecting prospects to multiple folks who are passionate about your cause), as well as a great testing-ground and pathway to board involvement.
• Meet one-to-one so you can ask questions to really draw prospects out. One I like is “Who was your mentor?” as it gives you an idea of what makes a deeper relationship in the prospects’ minds and hearts. You learn about people who took time to help and guide them. And as they recall these relationships, it puts them in a kind, benevolent frame of mind, making them want to give back, too.

6. Get Ready to Fulfill

What happens if you’re on “Shark Tank” and you get a big influx of capital? Suddenly you’ve got to fill orders—and you better be ready to jump on the opportunity! If not, your website may crash and your customers may be disappointed. They won’t come back. Retailers need to be customer-service focused; fundraisers need to be donor-centered.

Your job is to enable your donor to feel good about his or her philanthropic investment, not just at the point of commitment but long, long thereafter. This is how you’ll secure additional annual and major gifts, as well as legacy gifts in the future.

Tip: Put systems in place. Make sure your database and staff training enable you to follow through with your donor. If your prospect says “yes” to your proposal, you need to be ready to fulfill your promise to put the gift to work to make change happen. You also need to be ready to acknowledge the gift promptly and personally, and to report back on the impact of the donor’s philanthropy. It takes a team of folks touching base with your prospects, and each interaction must become part of your institutional memory. Donors get ticked off if they tell you stuff and you forget it. They want you to know them.

Tip: Think about your stewardship plan in advance. Track donor preferences and engagement points in your database so you assure the best, most personal stewardship experience possible. If you notice that engagement is diminishing, put in place new stewardship touches to ameliorate the situation. Things to track include:

• Events attended
• Volunteer activities
• Email/blog opens
• Email/blog forwards to personal network
• Clicks on links
• Communication preferences
• Social-media advocacy
• Website visits
• Inbound interactions (calls, stops by, emails, writes a letter)
• Soft credits—matching employer, foundation, donor-advised fund (a clue he or she will be a donor for many years; folks don’t set them up unless they intend to use them)

If there’s a moral to this article, it’s this two-parter: One, share 
simple stories with your major-donor prospects to bring your 
mission to life in a compelling fashion (watch “Shark Tank” to see how the best entrepreneurs do this), and two, use stewardship to 
uncover which stories will most float your donor’s boat. (“Shark Tank” contestants often have particular “sharks” in mind when they present, and they align their presentations accordingly). The better you know your audience, the better you’ll be able to tailor your proposal to their personal passions.

Making a dynamic major-donor solicitation is easy if you make it so. And impossible if you don’t know (and don’t think about) what you’re doing. Like anything else worth doing, it requires preparation. And this aspect of the process never, ever stops. Wherever you are in the process, from introduction to commitment to fulfillment, keep preparing. Keep practicing. Keep promoting. And keep being passionate.

Passion—yours and the donor’s—is what engages and secures commitment.