In this episode of Diamond Podcast, host Alfredo Diamond sits down with Jeremy Kean, owner of Kean on Biz Coaching Consultants, to discuss entrepreneurship, business growth strategies, and the future of AI in business.
The Journey of a Serial Entrepreneur
Jeremy Kean’s entrepreneurial journey began remarkably early—at just 13 years old, he started his first business as a disc jockey. With his parents both being teachers, Jeremy observed their work life and decided he wanted something different: “I just thought, man, what’s out there that doesn’t involve bosses?”
While his friends were focusing on extracurricular activities, young Jeremy was DJing dances, proms, and weddings, earning $1,000-$1,200 in a weekend. This early taste of entrepreneurship set the stage for a diverse business career spanning multiple industries:
- Mortgage and real estate business
- Financial sector/credit repair
- Digital marketing
- Fundraising (Suds Fundraising)
- All-natural products
- Apparel
- Streaming services
From Business Owner to Business Coach
After years of building and selling businesses, Jeremy found himself at a turning point when his business coach suggested he should start coaching others. Initially resistant—”I haven’t even figured out my own business yet”—Jeremy eventually embraced the idea in 2021.
“I got into business coaching… felt a little burned out and bored with building my own thing. I really like to help others,” Jeremy explains. What started as coaching evolved into consulting as he recognized that many clients needed more than just advice—they needed someone to help implement solutions.
Jeremy breaks down the difference between coaching and consulting:
- Coaching: One-on-one sessions with open agendas, focusing on mindset and systems
- Consulting: More structured, involving entire teams with phased approaches
- Agency Work: The “done for you” approach where Jeremy’s team handles implementation
The Value of Business Coaching
When asked about who seeks out his services, Jeremy explains that clients typically reach out when feeling frustrated or overwhelmed: “When the cup’s full, I’ve tried everything that I think I can try—what’s next?”
Many of his clients remain with him for years—his first client has been with him for four years. The relationship often evolves from coaching to consulting and then to implementing software, systems, and frameworks.
“Sometimes it’s coaching, sometimes it kind of scope creeps over into consulting a little bit. Sometimes it’s like business therapist,” Jeremy says with a smile.
Business Growth Challenges
For small businesses looking to grow, Jeremy offers valuable insight on a common pitfall: “You have to look at business in two sections—bringing it in and selling or converting, and then providing the fulfillment.”
He explains that scaling both sides simultaneously is crucial:
“I see a lot of times good product, good service takes off with a bang. The infrastructure is not there to handle that much in sales, so the backend falls, relationships fall.”
His advice is to properly plan ahead and ensure you can support business growth: “Having that plan ahead of time is super important because when you see, ‘Oh, I’m doing way better than expected,’ that can be good but it can also have some real red flags.”
Risk, Failure, and Resilience
When asked what advice he’d give someone afraid to take the entrepreneurial leap, Jeremy offers pragmatic wisdom:
“You got to look at what’s realistically what are you risking… Then take what you think you’re going to need, multiply it by three, and don’t do it until you have that.”
He shares that undercapitalization is the biggest problem he’s seen in 30 years: “They go off and lease a three-year lease on a building, build it out, do all that, and then three months in, they’re having trouble paying for inventory.”
Jeremy isn’t shy about discussing his own failures. He describes a crossroads where he broke his own rule about building infrastructure before expansion:
“I went okay, the right thing to do is ‘no,’ but go deep. And I went the other way, knowing darn good and well it wasn’t the right thing, but I was a superhero. I could do it. And it wrecked my world for a while.”
How did he bounce back? “Therapy, really. Hired a psychotherapist, made some tough decisions. Took a couple six-figure losses.”
Yet Jeremy maintains a philosophical approach: “If you lose six figures on two and you hit seven figures on one, you’re still at a really, really good position. If I can be like an MLB player and go one for three in the businesses and still come out ahead, there’s nothing to stress about.”
Work-Life Balance
With three children and multiple businesses, Jeremy admits that balancing work and family life is challenging. His strategy involves:
- Using the Pomodoro technique (55-minute work sessions with 5-minute breaks)
- Being diligent with calendar management
- Thinking of time as a 7-day plan rather than a traditional 5-day work week
- “Chunking” similar tasks together (coaching calls with coaching calls, client tasks with client tasks)
“When you’re a small business owner, it is your life,” he says. “I just make it a seven-day plan instead of five, which is your typical work week.”
Business Challenges in the Community
When asked about challenges facing local businesses, Jeremy highlights the issue of entrepreneurs taking their teams for granted:
“A lot of them get in the rut of ‘it’s working and we’re getting by’… but [employees] want to continue to further their growth as people in that role, maybe learn other roles.”
He emphasizes the importance of team satisfaction: “If your team’s not happy, your clients aren’t getting the experience that you think they are. So you need to do vibe checks on your team.”
The Future: AI and Automation
Jeremy is enthusiastic about the future of business technology, particularly AI. He’s releasing a book called “The Manimation Effect” about blending AI, human creativity, and smart systems.
He believes AI adoption is non-negotiable for business success: “If you’re not starting to adopt certain pieces of AI and automation, you are going to be left behind.”
To illustrate, he shares a striking example: “I’d say 6 hours would be sort of a mark for if I was racing somebody to put up a 5-out-of-10 rated website. I built one the other day—better look, better feel, better functionality—in six minutes with AI.”
His message about AI is clear: “Don’t let AI freak you out. Don’t let it intimidate you. Don’t let it pass by either.” He encourages business owners to calculate the time savings AI can provide and see the financial benefits.
Final Thoughts
As the podcast draws to a close, Jeremy acknowledges those who supported his journey, from his parents and grandmother to his business coach and others who contributed to his growth.
The conversation reveals Jeremy as not just a successful entrepreneur but a thoughtful coach who understands the psychological and practical challenges of business ownership. His approach combines innovative thinking with a realistic assessment of what it takes to succeed in today’s rapidly evolving business landscape.
Whether you’re just starting your entrepreneurial journey or looking to take your existing business to the next level, Jeremy’s insights offer valuable guidance on navigating the path to success.