Jason Webb

Public Speaker

Jason Webb is a Milwaukee-based public speaker, entrepreneur, movement leader, and advocate of racial reconciliation. He helped start several churches, Brooklife Church and Lakepoint Church among others, as well as several nonprofits such as Upstart Kitchen and James Place. Mr. Webb founded an organization, a network of churches that helped start 15 new churches in the Milwaukee area.

Where did the idea for your career come from?

Anytime I’ve helped start, whether it’s a church or a nonprofit, I really wrestle with three questions.
The first question is what is the local predicament? In other words, what are the needs of the area you’re going into? Not what you perceive the needs to be, but what are the actual needs of the people there?
Secondly, what are the unique resources that you have? Because even if you see the needs, but you don’t have the resources to meet those needs, you can’t meet the needs. So you have to ask yourself “What are the giftings of the people that I have, and also the financial resources available to me?”
Finally, you have to ask yourself “What is our driving passion?” In other words, what gets us up in the morning? I think once you start to wrestle with those three questions, then you come to this point of saying, “Okay, this is what we can start.”
When we started churches, the local predicament was – nobody was going to church. We thought the church was out of touch, but in reality, it was [boring]. We saw statistically that 83% of people weren’t going to church, so we saw a disconnect there. The next thing we looked at were our unique resources. “We had people who could engage people with everyday issues, not something that doesn’t seem to connect.” Then our driving passion was to help people in their lives, and so we combined those together.
Likewise, for nonprofits, we’d ask the same thing “What’s the local predicament?” Well, where we are at, in Milwaukee, there is a need for business opportunities for African Americans. So we realized our unique resources were the businessmen and women who could mentor. We also had financial resources where we could start a micro-enterprise business, which we did. Interestingly enough, it was a commercial space kitchen where food entrepreneurs could come in and rent out the space for a low cost. Then the driving passion was to bridge the socioeconomic gap between whites and blacks in Milwaukee.
Anytime I start something, I ask those three questions. I got them from a friend of mine, Will Mancini, who’s written on them. Those are really the three things that drive me.

What does your typical day look like and how do you make it productive?

My typical day starts early. I get up at 4:30 every morning. That’s a time for me to center myself, to get off on the right foot; in my faith/tradition, connect to God and just meditate, get in a healthy space. It includes helping my kids out with getting ready. I look at my day from a more holistic perspective than I used to. So I try to plan time for exercise, as well as relational time with friends. During the day, I try to break down my day into different categories of connecting with people that my organization serves as well as studying and then sometimes a time for writing.

How do you bring ideas to life?

That’s an interesting question because I’m not exactly sure how it always works out, but it does. I have a habit of writing stuff down. My brain is always firing. So any time I have a pen and paper next to me, I just write down whatever is going through my mind. I whiteboard a lot of stuff, just any random ideas. Whenever I have an idea, whether it’s for a talk or whether it’s for an organizational strategic move, I am whiteboarding all that. Then I go through it and edit it out as to what’s important, what’s not.
Then I also always ask people that I trust, “Hey, this is what I’m thinking. What is your thought on this?” Kind of like what I call my wise counsel of a few people that I always go to for advice. Because they’ll be able to tell me either, “Hey, that’s the dumbest idea I’ve ever heard,” or “Yeah, run with that and go with that.”

What’s one trend that excites you?

Well, I work with churches and nonprofits and am passionate about racial reconciliation, so in my industry, the trend that is the most exciting is that it seems like the church is finally engaging in racial reconciliation issues. We still have a long way to go. But the events of the last few years have finally woken it up to say, “Okay, this is an important thing to engage with.”

What is one habit of yours that makes you more productive as an entrepreneur?

I think one is to always be a learner. Throughout my career, I always found at least two or three people that were one step ahead of me, whether it’s in speaking, or in organizational leadership, and I just latch on to them. I ask them any questions that I have, I ask them to mentor me. I think the moment you think you’ve arrived, is the moment you stop developing. That’s really important – always see yourself as a learner.
Also, always surrounding yourself with people who are smarter than you. I think a lot of people want to be the smartest person in the room, but if you’re the smartest person in the room, you’re in the wrong room. You always need to be learning and not be afraid to have people speak into your life to develop you.

What advice would you give your younger self?

Slow down, like way down. Enjoy the moment. I was in such a rush to change the world that I forgot to enjoy what was right in front of me. I think entrepreneurs especially struggle with that. They’re visionaries by nature, and so they always want to go, go, go, go, go. Then in the midst of that, you can miss the beauty of what’s around you, whether that’s in your personal life or in your organizational life. So it’s really important to celebrate what’s already there. The people will appreciate you more and follow you more wholeheartedly if they see you slowing down to appreciate what you already have.

Tell us something that’s true that almost nobody agrees with you on.

I’m not sure. That’s an interesting question. My main training came when I was living in Kenya. I was really influenced by a few mentors of mine who had a very different outlook on life compared to the American way of life. One day they were talking about starting five new churches on one day and I thought, “You guys are nuts.” I was a pastor at their church. I said, “You guys are crazy.”
The person that I was talking to looked at me and said, “You know what the problem of Americans is? You live your lives by the motto, ‘Ready, aim, fire,’ and all you do is aim. You never actually fire. But we live by the motto, ‘Ready, fire, aim.’ We may make mistakes but at least we’re doing something.”
Ever since then, I’ve taken that as kind of a mantra in my leadership, to live by the motto, “Ready, fire, aim,” because you’re never going to be ready. You’re up against that with people, especially if you’re dealing with boards or other staff members, they want to see how your ducks are all on a row, and quite honestly, you’re never going to have them all on a row no matter what you’re doing. So at some point, you have to pull the trigger. I would rather go down trying to do what’s right than to just always be planning and never actually doing.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

It’s pretty simple, but read anything you can, listen to any podcast you can that’s helpful, and ask as many questions as you can. Again, this goes back to that learner mindset. The best leaders are the ones who ask questions and continually develop as people and as leaders up until the day they die. Because the moment you start to just relax and go off on what you know, that’s when and the organization becomes stagnant. It’s not going to do what it could do.

What is one strategy that has helped you grow your business?

One thing I learned is to push the decision as far down as you can in the organization. At one point I was handling an organization that had 250 staff members and I realized that if I just said, “Hey, this is what we’re deciding on this,” then people would have to follow because that’s their job. But the more ownership I can give away the better, because it improves people’s involvement in the vision of the organization and increases their ability to grow as leaders. Now, they may not make the decisions exactly the way I would like them to, but I’d rather deal with that than having people, who are really not in line with the vision and are not owning it themselves.
So, I think a mistake a lot of leaders make is that they don’t push decisions further down. You have to really wrestle with, “Okay, what are the only decisions I can make and how many decisions can I take out of my hand and give to the people that I say I trust?” and get it as far down the organization as you can.

What is one failure you had as an entrepreneur, and how did you overcome it?

This kind of goes back to the advice that I gave my younger self. I went too fast. Oftentimes, I burnt my staff out in the process. I burnt myself up in the process. For example when I have started the church and we were growing, we actually purchased a Wal-Mart and renovated it, moved into it and doubled in size right away, I said to my staff, “We’re going to start a new church out of this within a year, because I don’t want us too complacent”. So over this year we’re trying to catch up to our growth and dealing with this new facility, we also launched the new church out of ourselves. The church looked successful on the outside, but one-day l looked at my staff and they were just exhausted. I realized I had just pushed too fast, too hard. Even though it was a good thing we had done, it wasn’t the right timing. So understanding not only what is the good and right thing to do but also when is the best time to do it is really important.

What is one business idea that you’re willing to give away to our readers?

I would say focus more on your work culture than you do on your vision. I think it’s Peter Drucker who said, “Culture eats vision for lunch.” What I found out over the years was that I can have all the vision in the world but if the culture is tough, I have to put more effort into changing the culture of the staff and of the organization. If the culture is tough then it really doesn’t matter what the vision is.

What is the best $100 you recently spent? What and why?

I would say the best hundred dollars I recently spent was taking my kids out for dinner and a fun day. Any time I can spend quality time with them is money and time well spent.

What is the one book that you recommend our community should read and why?

A book Essentialism by Greg McKeown. It’s really about asking the question“What can only you do?” as an entrepreneur, or as a leader of an organization. Ask yourself “Based on who I am, the job that I have now, what are the couple of things that only I can do?” Then you give everything else away. That was a really important one for me to read.

What is your favorite quote?

One of my professors in grad school always said to us before he started every class, “Be who you is, because if you ain’t who you is, you is who you ain’t.” I think in leadership we often try to be somebody we’re not. We can never be successful at it. It will eventually corrode us as individuals. So really the important thing to do is to understand who you are, what’s the uniqueness you have, and lean into those. Just don’t try to be somebody else. Just be who you are.

Key Learnings:

  • Slow down. As entrepreneurs, we are always on the go, but it’s important to enjoy the moment and appreciate what’s already there.
  • Follow the motto “Ready, fire, aim”. You are never going to be 100% ready, so stop planning and take action.
  • Pay attention to the culture of the organization even more than the vision of the organization.
  • As a leader, focus on essential things only you can do and give away the rest of the tasks.
  • Accept the fact that you can not be great at everything and it’s okay, Just be you.