Lessons on Creating a Legacy

creating legacy

Far too often, Matthew O’Reilly would sit in the back of an ambulance, rushing a patient to the hospital but knowing full well that the patient wasn’t going to make it. And the patient knew it too.

Often, the patient – a complete and total stranger – would look Matthew in the eye and ask the simple question: Will you remember me?

I saw Matthew’s moving TED talk live in 2014 and his words have stayed with me. They were heartbreaking.

Many nonprofits are started by families who have lost loved ones, often as a result of a tragedy, a health issue, a violent crime, a terror attack. Far too often, these loved ones were taken far too soon.

And so today I want to introduce you to two folks, Kari Pepper-McKeone and Todd Crawford. Both started nonprofits following a personal tragedy. You really need to hear their stories.

They have lessons to teach those who stand in similar shoes. And that’s a whole lot of us at some point in our lives.

Kari’s and Todd’s stories can help us make sense of those times in all of our lives when we ask ourselves these questions. How can I make sure that some good comes from this tragedy? How do I make sense of this? How do I create some kind of legacy?

Or the question that so many have asked Matthew O’Reilly.

Will you remember me?


Todd lost his wife, Lisa Colagrossi, to a brain aneurysm in March 2015. She might have been saved had they known the warning signs. Four months after Lisa’s death, Todd secured a 501c3 and opened the doors of The Lisa Colagrossi Foundation, shedding light on brain aneurysms so others could be saved in time.

Kari lost her son Justin in a terrible car accident in August 2007. Kari and Justin were both passengers when her 16-year old nephew fell asleep at the wheel and the car flipped over. Kari started small. But seven years later, Kari secured the 501c3 for The Justin Pepper Foundation, an organization working to engage young people in community service. This was a perfect mission to honor Justin, who always did a lot of volunteer work. The foundation’s motto? Proof you are never too young to make a difference.”

Kari and Todd are both active members of the Nonprofit Leadership Lab, my online learning and support community for leaders of small-but-mighty nonprofits that I helped launch this spring. It was inside the Lab where I first met them both, and where they met each other.

And I’m so glad we met.

I had a lot to ask them about creating a legacy.


Kari: The accident happened amidst complex circumstances and it made the tragedy and grieving all the more complex. Sadness, guilt. So many emotions.

My ex- husband said something that stuck with me: “Justin was such good kid and so young that no one will remember him.” I couldn’t let that be true.

For the five years before his death, Justin donated all his birthday gifts to a children’s home. And so we started with a toy drive. It just seemed like the right way to spend Justin’s birthday that year.

Justin always did volunteer work. At his funeral, I was approached by a woman who had seen his photo in the obit. She told me he had painted her porch the year before and she enjoyed his smile.

My ex-husband and I started to look at places to donate money in Justin’s memory, but we had different ideas of places to donate. We did donate money and that could have been enough. But for some reason it just wasn’t.

I began researching guidelines for starting a nonprofit.

Todd: I wanted to spare other families from the heartbreak and devastation that my two boys and I experienced. I wanted to arm folks with information to be better informed and to let people know there are choices we didn’t know we had. Lisa had warning signs and we dismissed them. We didn’t know.

Lisa’s passing was a pivot point for me. I had a choice. I could stay the course, as I always had, or take this pivot point and head in a new direction.


Kari: I should have done more research. I was negotiating a lot of family emotions and dynamics. We started as a local organization honoring Justin but I wanted to expand – to an organization that worked with kids who never knew him and to promote community service among young people.

Todd: Three weeks after Lisa’s passing, I began researching existing organizations. I traveled cross-country and met people. I scrutinized business plans.


Kari: Some days I don’t think I am doing anything right. I have a vision and just can’t seem to get the support I’m looking for to make it happen. That said, one thing we did right was to make our scholarship unique. We didn’t look at financials or at academics. It’s all about volunteer work. The student doesn’t even have to be going to college; they can attend any secondary school.

Todd: I did my homework. I invested time in understanding the sector to ascertain if there was a big, clear identifiable need. There was.

Secondly, I treated the Foundation like a business, not a hobby or a family foundation. Next, I created an independent organization with no family members involved.

Third, because of Lisa’s role in the media [Lisa was a popular TV reporter in New York City], we were able to secure press and visibility. We just launched the first public service announcement to seed the foundation’s name through awareness about brain aneurysms. Lastly, brain aneurysms touch the lives of many, including celebrities. PSAs with Whoopi Goldberg and Mario Batali are in production.


Kari: Where do I begin? The name: HUGE mistake. Not the Justin Pepper part, the ‘foundation’ part. Folks think we give away money.

Secondly, my ex-husband and I were not always on the same page – strategic differences. Should we change the name and take Justin’s name off? I thought this was worth considering and Jim was adamantly opposed. Jim was a VP of the Board and I would make that choice again but it created challenges.

Next, I didn’t know much about nonprofits and set up our website and email addresses as .com instead of .org. Lastly, maybe we should have used the insurance money to hire someone to get the organization going and off to a good start.

Todd: I moved very quickly. I would have taken more time to build the organization and develop a strategy for long-term success.

We knew absolutely nothing about fundraising. The organization is entirely self-funded (by me.) We did not tap into nonprofit experience in certain areas. We could have been more efficient and disciplined as a foundation.

I may have made a mistake with the name. I thought about Susan B. Komen and I knew that women are at least 50% more likely to develop aneurysms than men. I thought there was an opportunity to leverage Lisa’s story for visibility. But I often wonder if we should have instead launched The National Brain Aneurysm Society. 


Kari: I don’t have regrets about starting the organization but think about walking away often. The organization is totally reliant on me and I’m burning myself out. It’s hard to find down time and then I feel guilty I’m not doing more. I hope I will not have “founder’s syndrome” when it’s time to step back, but I’m afraid I might.

Todd: It is a double-edged sword. The work is more gratifying than any job I held in the corporate world. And it makes me feel connected to Lisa every day. But the constant reminder of your loss can be really hard.


Kari: I don’t know – it wouldn’t be the same. Fundraising has been a big challenge and I put a lot of my own money into the work. It’s very hard for me to ask anything of anyone, especially money. I’ve never asked.

Todd: This is my biggest concern because while our work is making a difference, we are not raising money from outside sources. We have to build the case for support, define and develop the narrative better to compel people to donate and develop diverse fundraising strategies.


Kari: Think long and hard about whether you should start a standalone organization. I am a believer in fate and feel this is what I was meant to do. But I think anyone who finds themselves in this tragic place needs to really look at what they can handle and take on. And what they can’t.

Finally, find something your loved one did well or loved to do and direct your energies there. Do something that will help you remember the attributes you loved and admired about your family member. It can be more than an organization named after your loved one. S/he can live on in so many ways.

Todd: Look at and think about the major pivot point in your life you have just experienced. Determine if you are able to / want to pivot. Allow yourself time to grieve and process as you go.

There is no greater gift than the work you do to honor your loved one’s life and to advocate for the cause of their passing.

You are cut from a very special piece of cloth. You have chosen to open yourself up in every way, exposing yourself and your family and your grief to the entire world while attempting to help others at the same time.


It is clear that Kari and Todd are cut of a very special cloth. I hold their stories with care and am ever so grateful that they were willing to share them.

Matthew O’Reilly mentioned something else about creating a legacy in his TED Talk that stuck with me and seems fitting to end with. In addition to wanting to know they will be remembered, those facing imminent death also want to believe their lives had purpose. Meaning.

As I consider the stories of Kari and Todd, as I think about the thousands of men and women who have and will face these unimaginable tragedies, this is what sticks.

And that is the real lesson Kari and Todd teach us. They have navigated unimaginable waters and every day, they carry their grief with them to the office in the service of ensuring that Lisa’s and Justin’s lives had meaning.

Here’s hoping that the stories of these special people offers comfort and solace to those who stand in these sad shoes. Or those of us who stand with them.