Jimmy Odom, WeDeliver

Founder: Jimmy Odom
Company Description: WeDeliver brings on demand delivery to neighborhood businesses.
Company Site: http://www.wedeliver.us/
Date of interview: October 2014

Jimmy Odom, We Deliver

Jimmy Odom, We Deliver
Art by Luke Martin of What the L?! comics and more

Jimmy wasn’t my first interview, but I wanted to lead with him for a few reasons. Firstly, because it was this coffee date that gave me the idea of the site name. But other than that, he is just so electric and passionate – it seemed like an obvious opening post.

On figuring out what he wanted to do:

“I have a different view on life and careers than most people. I think if you’re good at one thing, you can be good at anything. Throughout my life, I have come across things that I was really passionate about and that I really enjoyed. I’m driven by passion. That’s what gets me excited, that’s what gets me up every morning. It’s totally random – it touches my heart and I become passionate about it.”

(You can read from Crain’s and Chicago Sun Times that he has a diverse past exploring careers in culinary arts, screenwriting, and even emergency medicine.)

On entrepreneurship and ideation:

I asked him if he always wanted to be an entrepreneur. He looks at me and explains that it wasn’t about wanting it, he has just always been one.

“I’ve always done it. I was that kid on my block who organized all the basketball tournaments. I was always doing it, I just didn’t know there was a term for it. I do wish someone had identified me as I grew up. I’m learning now, but I think it could’ve honed my skills a little more at an early age. I’m so glad that entrepreneurship is actually being encouraged in the school system now. Not everyone is going to be an entrepreneur, but we all have the ability to be one.”

In terms of his ideas – they “just happen”. He doesn’t have a special process for it, he doesn’t sit around and brainstorm and they’re not always triggered by anything.

“They just come. It’s been like this all my life. They just come. I could be sitting at home doing absolutely nothing that has to do with my idea. Just happens.” (Good luck trying to replicate that, people.)

On coming up with WeDeliver:

While he was working for Apple (a job he says he absolutely loved), he went to Stanford Startup School and came back on an inspirational high.

“I came back and I was just on fire for entrepreneurship, and on fire for technology. Being surrounded by some of the smartest people in the world… that was electrifying and invigorating.” 

He knew he wanted to build something, but it was just a matter of what. He thought of it after his mother asked him to pick up a prescription for her.

“The pharmacy was right next to the pizza delivery place. It just didn’t make sense. Why doesn’t it (on demand delivery) exist? Let’s build it. Simply put- it was just the right place at the right time and I knew I wanted to do this.”

On building a team:

Jimmy doesn’t consider building a team to be a traditional hiring process.

“If you look at the creation of the planets – there are just interactions, collisions and chaos. And from chaos, comes order.”


Illustration by Alexa Tang

Illustration by Alexa Tang

“Developing a team in the early stages – those were just collisions – meeting people in the environment and seeing who you stick with through gravitational pulls. That’s how we all met. It wasn’t probably until employee 15 that I started to think more strategically about who comes into the company and what role they will fill. That is something I had to change in terms of how I look at growing the company.”

On getting customers:

“I literally went from door to door down Chicago avenue.”

Now that he has customers, his approach is still the same except that WeDeliver is getting a good amount of referral business as well. “If you want to build a business that empowers local businesses you need to get out, you need to talk to them, you need to see them, you need to meet them. I like to have a relationship with you.”

On handling rejection:

“Each time it was good to reinforce that I’m not doing this to get into an event, I’m not doing this to get into a competition, I’m doing this because I see this business growing and I like my customers. I love what we do. Those other things are ancillary, they’re extra. It’s not the substance of the cake – it’s just frosting. It was so important for us to get back into the right mind set. It is all a mindset and how you think.”

(WeDeliver did NOT get into Tech Week or Tech Starters the first time around.)

On advice ‘they’ don’t tell you:

Apparently it is all about trusting yourself and learning from the right sci-fi hero.

“It’s so important for entrepreneurs to truly trust their instincts – to believe in themselves. We look at those that have built companies and think that whatever they know is better than what I know, whatever they’ve done is better than what I’ve done. I’ve met a ton of mentors over the last 2 years and each potential mentor comes and assesses a problem as if they have first hand knowledge of everything. You see something others don’t see – that’s why you’re the innovator. You see further down the road and you see what others don’t see – or else they would have built it. Trust the vision. Others can help shape it, but you have to trust your vision.  If you can align mission, vision and purpose with metrics – then some really interesting things happen.”

“I find inspiration everywhere.”

“Do you watch the show Heroes? Two of the most powerful characters of the show are Sylar and Peter. Sylar has to be hands on and dirty to accumulate abilities and become the all powerful villain. Peter just has to be next to you – just in your presence and he can get your ability. That’s what I want to be like. As an entrepreneur, I want to surround myself with amazing people so that the more I’m around them – I can see their skill set, see what makes them special, learn from them, and make them part of my team.”

“‘Become like Peter Petrelli.’ – We’ll make bumper stickers of that.”

Jimmy starts telling me a story after I’ve stopped recording and while he’s grabbing for his iPhone. He tells me that yesterday he left his iPhone on the train. After realizing he left it, he begins to track it via the GPS in his phone. He continues to drive next to the train that has his phone and realizes that his phone got off the train and has gone to an actual physical address. Against his wife’s advice, he decides he will see this to the end. He walks up to the door, rings the doorbell, asks for his phone back, gets it back and goes on with his day. I think this story represents his general spirit – he sees it, he cares about it, he goes to get it.

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