Trust, Timing, and the Long Game: Fundraising lessons from Tyler Bacon

Tyler Bacon, Vice President of Sales (right), with Brantley Boyett, founder of Giving Docs

When I worked at JUF in Chicago, I was pitched everything.

-Insurance tools that promised to raise millions.

-Marketing platforms guaranteed to unlock millions.

-Websites that would, surprise, raise millions.

Most of it blended together.

One person didn’t.

Tyler Bacon.

It took Tyler more than one visit to earn my attention, and even then, it wasn’t because of a demo or a slick pitch. It was a masterclass in sales without ever feeling like sales. No pressure. No urgency. Just thoughtful follow-up, real curiosity, and genuine connection over time.

Looking back, it’s exactly how great fundraising works too.

The Sale That Didn’t Feel Like a Sale

Tyler never pushed. He respected timing. He checked in without hovering. He built trust first and let decisions come later. When we eventually did move forward, it felt natural, not transactional.

Fast forward several years. We reconnected casually. Selfishly, I was reaching out for advice as I started my own company. Somewhere in the conversation, I learned something I hadn’t known before.

Tyler had cancer.

Strength, perspective, and resolve — Tyler during treatment

He had been battling leukemia, fighting, winning, and recovering, while still showing up professionally and personally. He didn’t lead with it. He didn’t center it. He shared it in the context of family, life, and perspective.

And suddenly, everything about how he talks about donors made more sense.

When Fundraising Stops Being Abstract

Tyler’s donors weren’t theoretical. They weren’t names on a list.

They were blood donors, literally keeping him alive.

That experience fundamentally shaped how he sees philanthropy. Fundraising, at its core, is about people, intention, and action. It’s about showing up for one another in moments that matter.

It’s also why I dare anyone to watch Tyler’s story from the UCLA Blood and Platelet Center and not feel something shift.

That perspective shows up in everything he does.

Today, Tyler works at Giving Docs after many years at Crescendo and as a partner in a small consulting practice, where he focused on strategic fundraising planning for major gift programs. And true to form, he’s still radically transparent.

He says things like, “We’re not right for everyone, and that’s okay. I tell prospects that.”

That alone makes him worth listening to.

Planned Giving Has Changed, and Tyler’s Been Watching It for 20 Years

One of the biggest takeaways from our conversation was just how much planned giving has evolved.

Twenty years ago, for many planned giving programs, the work leaned far more technical than relational. Acronyms. Legal language. Tax charts.

Those elements still matter. They always will. But what’s changed is emphasis. It’s more relational now than ever. Organizations are learning to show up for donors with greater intention, focused on service rather than solicitation.

In a world with more charities, and more noise, than ever before, the organizations that break through aren’t the loudest. They’re the ones that listen, guide, and serve donors with clarity and respect.

Donors don’t give because you explained a charitable remainder trust perfectly. They give because they feel connected to the mission, to the people, and to the impact they want their life to have.

As Tyler put it, and I love this, “People buy emotionally and justify logically. Donors are no different.”

That shift, from transaction to relationship, is everything, especially in planned giving.

The Bridge Between Intention and Action

One insight Tyler comes back to often is the gap between what donors intend to do and what actually happens.

Research consistently shows that a meaningful portion of Americans say they would consider including a charitable organization in their estate plans, but only a small fraction ever follow through. The difference isn’t generosity. It’s friction.

Most people want to do something meaningful. They just don’t get the right support, clarity, or timing. As Tyler puts it, legacy and endowment efforts exist to build a bridge between intention and action.

• Not by pressure.

• Not by urgency.

• But by guidance.

And that bridge doesn’t look the same for every organization.

What matters most isn’t size or sophistication. It’s whether an organization is willing to show up consistently for donors who raise their hands. To listen. To follow up thoughtfully. To treat curiosity as a moment of trust, not a transaction.

Some organizations are further along. Others are just beginning. Neither is wrong. They’re simply at different points on the journey.

What Effective Programs Have in Common

When Tyler talks about organizations that see success over time, he doesn’t point to flashy tactics or one-off campaigns. He points to fundamentals.

1. Invest in long-term relationships.

2. Create clear pathways for donors to engage when interest arises.

3. Follow up with care and intention.

4. Resist “spray and pray” in favor of relevance and respect.

In other words, they build systems that support donors, not just solicit them.

That philosophy is deeply aligned with Giving Docs itself, a platform founded by attorneys, informed by behavioral science, and shaped by real fundraising experience. It exists to remove friction, lower barriers, and help organizations meet donors where they are, with clarity and confidence.

A Case Study That Says It All

One example Tyler often references comes from the American Cancer Society.

Rather than delivering a single, generic message, they created distinct experiences.

-One for patients.

-Another for general supporters.

Same mission. Very different language.

Why? Because lived experience matters. Patients engage with a mission differently than supporters. When communication reflects that reality, engagement deepens.

Too many organizations still rely on one-size-fits-all messaging. The ones that slow down, listen, and speak to donors like humans, rather than audiences, build stronger,

sustainable legacy programs.

Why This Story Matters to Me

I’ve known Tyler for a long time. Our relationship started professionally and became personal, like the best ones do.

What I appreciate most is his consistency, honesty, and refusal to oversell. Tyler knows that legacy and endowment work is the long game, one that requires patience, trust, and real stewardship.

That belief shows up in how he works, listens, and shows up for the organizations he serves.

And the nonprofits that embrace that same mindset?

They’re in it for the long game too.

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I help nonprofits raise more money through education, coaching, and strategic planning. I also lead high-impact professional development, coaching programs, and retreats for companies of all sizes. If you’re ready to strengthen your fundraising strategy, turn board members into advocates, or build a comprehensive legacy giving program, let’s talk.