Interview with Parent and Entrepreneur James Oliver Jr.
Interview with Parent and Entrepreneur James Oliver Jr.

The ParentPreneur Foundation recently gave $10,000 grants to 10 grantees. We spoke with founder, James Oliver, Jr. about his experience of being a parent and an entrepreneur, and why he's specifically supporting the next wave of Black businesses.


How did you get started?

Back in 2013, I was working on WeMontage. I’d cleaned out my savings to build the alpha version. I was living in Northeast Wisconsin, 1,000 miles away from my family and pregnant wife. I was lucky enough to get into a startup accelerator, and I knew by virtue of that, I’d have the credibility to have conversations with investors to raise the capital that I needed desperately to launch the business.

My kids were due at the end of March, which aligned perfectly with the end of the accelerator. But two days before the start of the program, they were born, three months premature. They weighed two pounds apiece.

The accelerator was a two hour drive each way. So I'm in this accelerator, going back and forth to the NICU, waking up every morning at 2am because I couldn't sleep from the stress of it all, grinding to build a minimum viable product.  I cried every day. You could have walked up and said, 'Good morning, James!', and I would have started crying, I swear to you.

Fast forward to Demo Day in April. I was about to go on stage to present to a room full of potential investors to raise $250,000. Right before I went on stage, I got a call from one of the angel groups that we pitch to. He says, 'We're going to fill your whole round.' And I asked, 'What do you mean? He said, ‘We're giving you $250,000.’ And I just dropped on my knees. I just thanked God and cried.

I think the moral of that story is: We are stronger than we know. You must be persistent and resilient to get what you want in life. Thankfully, my kids came home, and now they're doing great. So I started a business.

Then I wrote a book, 'The More You Hustle, The Luckier You Get: You Can Be a Successful Parentpreneur', which was inspired by a blog that I started, 'trepLifeDad. I wrote the book to inspire the millions of people who are parents and entrepreneurs around the world. After publishing the book in 2017, I had an idea that one day, I’d sell my business, take a million dollars of my own money, and start a foundation.

The More You Hustle, The Luckier You Get: You CAN Be a Successful Parentpreneur
THE REALEST BOOK ABOUT ENTREPRENEURSHIP YOU’LL EVER READA story about persistence, resilience, and faith. Being a parent is hard, and so is being an entrepreneur. But being a Parentpreneur? Well, that’s a whole new level of crazy! This book takes you on a journey as James, a new dad of twins, and fo…
James Oliver Jr.'s Book is Available for Purchase Online

This March, right when COVID-19 was starting to ravage the world, I had a chance coffee meeting. These guys said to me, 'Why are you waiting to launch this foundation? Why don't you do it now?' And I thought, 'Yeah, now's the time! Do it!' Of course, I had no idea how the hell I was gonna do that. But I was thinking, 'God's gonna help me figure this out somehow.'

I started writing articles about how I was starting a foundation. Then George Floyd, Breonna Taylor, Ahmaud Arbery, and all this other foolishness happens. I had a neighbor, a couple houses behind me, terrorizing my girlfriend and me for no reason. On two separate occasions, I had to call the police on her and get a trespass warrant against her. But the damage was done, because now I don't feel safe in my home. In my backyard, I'm all squirrely if there's any noise.

After all this happened, I said, ‘You know what? This foundation is for Black people.’

How did you get support to launch?

The organizers of the accelerator I went to were super hustling. They reached out to Brad Feld and David Cohen, who are the co-founders of Techstars, and got them on a Google Hangout. Each one of us got to ask a question.

Then I subscribed to Brad's blog and began to engage with him. I didn't have any intention of building a relationship, but I liked him and his content. He started engaging with me, and it seemed like he liked me too! He bought a copy of my book and reviewed it on his blog. He loved it! The relationship has been building organically since.

In the last several months, I've come to regard him as a friend. He reached out to me out of the blue and referenced ParentPreneur in an article he wrote.  When we talked, he asked, "What two projects are you working on, involved in Black racial inequality, that I could put my time, money, and attention to?"

Besides writing a check, he helped me frame my thinking properly about my foundation. He's a person who knows how to get things done. One of my favorite books he wrote is 'Do More Faster'. People like Brad move quickly. It's not all this dithering about, only pretending to be influential. He helped me create an operating plan. We worked on it together and since we co-created it, he liked it, and then he owned part of it.

Brad got to see how I think, how I communicate, how I execute. He liked it all. He was confident in giving us $50,000 and extending his social capital.  As I wrote about in this article, I wouldn't know about Open Collective if it weren’t for him. Because he introduced me to someone who explained, "Oh! No, no, no, you don't need to worry about the IRS and the 501(c)(3) process. You can start taking contributions that are tax-deductible tomorrow." And I said, ‘Wait, what?’ And he said 'Oh, yeah, don't worry. I'm going to introduce you to Pia.' My mind was blown.


Wealth Inequality Gap
Wealth Inequality Gap

Everybody knows about the family wealth inequality gap between Black families and white families. The Federal Reserve posted this chart showing the median wealth of the white families is 10x Black families. Well-to-do Black families (75th percentile) are lower than the median of the white folks!

In addition to the wealth gap and the lack of resources, the social capital gap is possibly even more insidious. We, as Black people, cannot execute on our good ideas, because we don't have the social capital. Because of a lack of social capital, we don't even know what's possible.

Through Brad's social capital, he connected me with the 1k Project, who connected me to Open Collective. All that happened through a quick email introduction. On Thursday, he sent the email to Pia. Tuesday, we were on a zoom call. Wednesday, we were set up on the Open Collective Platform. Thursday, I have a $50,000 tax-deductible donation from Brad.

My point is: if I hadn't talked to Brad, I never would have known that was an option. I'd be sitting around here big mad about the stupidity of an IRS 501(c)(3) application wait time.

Why support parents specifically?

Going back to that graph of wealth inequality, it shows that we don't have the resources. We don't have a family member that could spot us $100 grand until our businesses get off the ground. If you have children and you're an entrepreneur, the pressure is more acute.

It's unlike just being a regular young hoodie-wearing dude living in your mama's basement working on a startup. The mental health issues, the relationship issues with your partner or spouse, the parenting issues, the affect on the children. It's a unique challenge. And then the whole social capital thing we talked about.

I am intentionally working to help these people be the best entrepreneurs they can be, by bringing tools and resources. Not everyone will get a grant, because we just don't have the money. We're not the Bill and Melinda Gates Foundation. But maybe we can give you a $50 gift card from a national restaurant chain. I'm working on something like that now. Then, once or twice a week, you can get a meal to feed the family and not have to reach into your pocket.

I'm waiting for Emory Psychiatry to get back to me, so I can work out a deal to pay for therapy sessions for people in the ParentPreneur community. I want to say 'Hey, guys, if you want to get some free therapy hour long sessions, we already paid for it. So call these people.’

This is the kind of stuff that we're doing. How great is that?

What trajectory are you hoping to see?

I don't know much about foundations and philanthropy and nonprofits, but I do understand that people want to see how you measure impact.  I have to figure that piece of it out.

My impact will be to improve their businesses, their mental health, their relationships with their spouses and partners, and them as good parents, for them to raise delightful children. That will be our contribution to humanity.

How do you measure that? It'll be great if everyone in our foundation’s social network improve and the kids do well, and their relationships with their families do better. They can anecdotally speak to the improvement in their mental health.

I'm taking a holistic 360 degree view. It's not just, ‘Here's $1,000 for your business.’ No, that's just part of it. It's so much more than that.

James Oliver Jr. pictured here with his two children: his "twin-nado"
James Oliver Jr. with his "twin-nado"

My vision is to be able to give $10,000 grants to a minimum of 100 people. That would be a million dollars a year. That's where I want to be.

Then, to be able to help a couple thousand other people with resources for their businesses, their lifestyles, as a parent, and a variety of other things, to impact the lives of more people. Some grantees will have new projects coming down the pipe. They need the money for this, they need the money for that, to support their business. They can use the money for whatever they think will help make them a more effective parent and entrepreneur.

What do you want the world to know about the ParentPreneur Foundation?

The Parentpreneur Foundation exists to empower Black people to be the best possible parents and entrepreneurs. That's it.

It's all on the website. Visit! If you're a Black ParentPreneur, you can join our community. The grants right now are going to Black ParentPreneurs who have eCommerce products, simply because that's my passion. We can't help everybody so I have to narrow it down some. But anybody who's a Black parentpreneur can join and get the other resources that we have.

We also need corporate partnerships, so we can provide resources to beneficiaries in our community. And fundraising: We need people to make contributions so we can continue with this really important issue.


IG: @ParentPreneurFoundation, Twitter: @ParentPreneurF

Support the ParentPreneur Foundation now!

Read the Full Interview Transcript here.