James McKinney describes himself not simply as a “serial entrepreneur” but as a “failed serial entrepreneur.” By his count, he has four startups that did not make it, although from each failure he learned something.
“I did not believe it was me, I did not believe it was my skill set,” he told me during an interview for my podcast, Back Yourself. “But I saw other successful entrepreneurs and thought, Why are they winning and I am not?”
Rather than retreat into his failure, he reached out to those who he saw as individual success stories, meeting them for coffee or lunch and learning from them by listening to what they had to say about entrepreneurship. They were only stories of success, but they were inspirational — and as he recounted them to friends and associates, he was constantly told that he should record and share those success stories.
Soon, McKinney was talking to really big names — like the founder of E!, who went from living in a gutter to selling the entertainment news channel powerhouse for $3 billion.
“People kept coming to me and saying, Do you have this in a podcast?” he said. McKinney was already an avid podcast listener, and with enough people asking him for recordings of his interviews, the solution to his next job seemed rather obvious.
The Backstory: How McKinney Went From Electronics Repair to Youth Pastor
Let’s just say that McKinney has a rather diverse background.
He attended California State University at Fullerton and earned a bachelor’s degree in accounting and finance, then a bachelor’s in business administration. Prior to that, he was an electronic equipment repair specialist attached to the Marine Air Wing of the United States Marine Corps. While in college he was a financial analyst for Pulte Homes, the largest homebuilder in the United States, and then a youth pastor overseeing a church’s middle school student ministry.
For a bit more than two years, McKinney was an accounting transaction manager for RREEF, and later president of sales and business development for All Business in Long Beach, Calif. He was director of accounting and operations for NexGen Digital and the president of California State University Fullerton Business Titans Alumni Chapter. He held two roles at The Walt Disney Corporation — asset liquidation and business operations manager — and was then vice president of strategic solutions for Vision Media Management.
In 2008, he founded Simple Deal, which was meant to turn your phone into a TV remote. He was also director of the Santa Clarita chapter of Startup Grind, which hosted speakers, and then vice president of strategic growth for Status Not Quo. In 2019 he created The Startup Story, a weekly podcast that examines the entrepreneurial journey, and in 2020 founded Grindology, which sends coffee, a mug, and an entrepreneur magazine to subscribers each quarter.
Making a Better Podcast: Ask the Right Questions
Like many podcast fans, McKinney was an avid listener of the NPR podcast How I Built This. But while fascinating, the show also often missed the mark: Since the interviewer is a journalist and not an entrepreneur, there were often many obvious questions that should have been asked but weren’t.
“I was in my car driving to work screaming, Why didn’t you ask this?” he said. That was the final straw — his own podcast launched in January 2019.
The end of 2019, of course, was an interesting time to found a podcast. Soon, McKinney was looking for a way to monetise the operation. His first idea, a founder’s meetup, was killed by COVID-19 lockdowns, but he quickly pivoted to an online event. While he made little money from the event, his listenership has grown four-fold and more.
How to Monetise Your Brand
One thing that McKinney learned from the demise of his entrepreneurial meetup, and which was backed up by his conversations with other founders, is that you need to look outside of sponsorships and advertisers to monetise your podcast.
“You should not be brokering your audience, you need to figure out how to leverage that directly,” he said.
For McKinney, that was coffee and the founding of Grindology — a natural fit since almost all entrepreneurs drink it.
5 Tips to Build Your Audience
McKinney did not set out to build a huge audience — he truly wanted to talk to and learn from entrepreneurs.
Almost by accident, he interviewed a homeschool teacher, and the podcast was promoted by Kylie Jenner, and his downloads skyrocketed. That showed him the value of building a brand.
He also built an audience by being authentic and transparent, and by:
- Creating something that founders want to share
- Focusing on the founder’s youth story, something few podcasts do
- Encouraging advertisers to leave reviews, which he reads on his show
- Creating a consistent show where listeners know what to expect
- Being in tune with what society is talking about — i.e., including a diversity of founders
Entrepreneurship is not easy, McKinney agrees. The headlines will have you thinking that it’s easy to get rich, and that venture capital will help get you there. There are much easier ways to make money and become successful, he said — ensure you are prepared for a career of problem solving.