Jason Webb is a Milwaukee-based public speaker, movement leader, strategic thinker, and a results-driven executive with a proven track record in fundraising. He has helped start multiple churches and non-profit organizations, ran their multimillion-dollar campaigns, and oversaw a complex $12.5 million budget at his last organization. Mr. Webb is also a philanthropist, passionate about helping those in need on a global level.
Jason, Thank you for talking with us. Being involved in philanthropic activities mean more satisfaction at a personal level. However, there must be a few off days too. Tell us about your best and worst days at work.
Thank you for having me. I would say that the best day is a day where I can do a couple of different things. One, just a chance to dream and create a vision for the future, for the organization I’m leading. To have a chance to think, “What’s next? What hills can we climb next in our process?”
Then secondly, just a chance to write – I love writing – and a chance to express myself that way. Then finally, I would say with a good day, being with people is always something I love to do. Whether it’s leaders within an organization or just really anybody on my staff, that’s a good day for me.
The worst day is any day that’s just filled with meetings, especially budget meetings, meetings that are going through heavy details that may not be my strong suit. Meetings tend to wear me down.
What are the projects that you most enjoy working on?
Anything new, any startup, any new initiative. I love to start things. I love to not only start things but take things that may have grown stale or stalled and say, “Okay. How do we bring this to the next level?”
Right now I’m helping a small church nearby, just think through, “How do we get past these growth barriers that we seem to be bumping up against?” Anything that really can either start something from the ground up or push something that’s been existing for a while to the next level.
What was your biggest ‘a-ha’ moment?
That would be learning I could say “no” to things. It seemed like a simple thing to learn and I wish I would have learned it earlier in my career but I felt I had to be everything to everybody. In the process, though, if you try to be everything to everybody, you end up being nothing to nobody. It’s just this endless cycle you find yourself in. You can’t please anybody and you’re just growing frustrated, and all the work you’re doing tends to be more mediocre than anything.
I think it was Jim Collins who said, “Good is the enemy of great.” I think a lot of times you say yes to good things when you really need to say yes to the great things, the things that you’re really good at. That took me a long time to learn. Sure a lot of trial and error but finally I was able to figure out, “It’s okay for me to say no to certain things so that I can give a better yes to the things that I’m really good at.”
We know that you had a life-changing experience in Nairobi, Kenya. Tell us more about your experience there. Also, what has been the most important part of your professional journey?
I spent three years in Nairobi, Kenya. They’re the formative years of my career. I was 25 when I went there. One, I had to take a learner’s posture because I was learning culture, but two, I was mentored by a guy who just told me, “Hey, I’m going to take you under my wing. For the next three years, I’m going to teach you everything I know. You’re going to follow me everywhere I go and do everything I do.” That’s where my passion for the church and starting new churches grew because the church I worked at in Nairobi, Kenya now has started hundreds of new churches.
My passion for social issues grew there as well because I started to work with ex-prisoners, girls who needed schooling but they’re caught in tough economic situations, street boys, and other marginalized communities. That’s where I started to open my eyes to the social needs of the city.
What would you do with unlimited resources?
Probably a lot of different things. The main thing I would want to do is fight and break down system injustice. I live in Milwaukee which is one of the most segregated cities in America. I would love to use unlimited resources to bridge the economic gap between African Americans, Caucasians, Latinos, Asians, and really break that gap. I’d love to see the educational gap in our city be closed as well, resourcing cities and schools that way. Milwaukee is ranked as the worst city for African American males to grow up in, so I’d love to put resources towards that and to change that story.
When was the last time you totally lost yourself in doing something?
Probably even just this morning. I’ve been writing some of my own journey and some painful parts of it but also some good parts of it. I think anytime you get an idea and you can run with it especially in a creative way, whether it’s writing or whatever the creative way people express themselves, you tend to get lost in it.
What do you do when you’re not at work?
The main thing is I chase my kids around. I have four of them so they keep me on my toes. They’re great and they’re fun and they’re crazy. I also love playing and watching sports. I love to read. I love to spend time with friends just over a cup of coffee, just sharing their stories, inviting them into my story as well.
How do you feel you make a difference in the world?
I think this has changed for me. I used to think it was by creating big organizations that were doing great and grand things. There’s probably some truth to that. But recently I’ve realized, as simple as it sounds, it’s just by loving people well by being in their lives and walking alongside them, pouring yourself into them, and allowing them to pour themselves into you. Especially for me, how do I make a difference in the world? For me, it’s with my four kids. Forget everything else I do with my career. If I just love my kids in the best way I know how, imperfectly as it may be, they will be my greatest legacy. So that has shifted for me and that’s really where I want to make my difference in the world.
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