logo
episode-header-image
May 2025
27m 9s

Choosing Entrepreneurship Changed Everyt...

Kelly Kennedy
About this episode

In episode 239 of The Business Development Podcast, Kelly Kennedy reflects on the pivotal moment that led him to leave a stable, decade-long career and choose the uncertain path of entrepreneurship. Triggered by a tough boardroom conversation during the height of COVID-19, Kelly shares how that moment became the spark that launched Capital Business Development and, eventually, this very podcast. He opens up about trading security for freedom, the drive to make a greater impact, and the mindset shift it took to finally build something of his own.

This episode delivers powerful lessons from Kelly’s journey—breaking down the illusion of job security, the importance of taking action before you're ready, and the real truths about building a business from the ground up. It’s a raw, motivating conversation filled with encouragement for entrepreneurs at any stage. If you're wrestling with the decision to leap, this episode might be the push you've been waiting for.


Key Takeaways:

1. Sometimes the hardest conversations become the catalyst for the biggest breakthroughs.

2. Entrepreneurship starts when you realize employment isn’t as safe as it seems.

3. Freedom of time, purpose, location, and income is worth the risk.

4. In the early days, your effort is the business—there’s no backup engine.

5. Consistency beats talent, motivation, and passion—every single time.

6. You’ll overestimate what you can do in one year and underestimate what’s possible in five.

7. Your brand is what people say about you when you’re not in the room—build wisely.

8. Version one will likely suck. That’s the price of building something great.

9. The best opportunities won’t be the ones you planned—they’ll be the ones you’re ready for.

10. There will never be a perfect time to start. You create the right time by moving.


Ready to build your business development engine? Join the next Business Development Mastery Accelerator and start turning strategy into results.

Secure your seat now

Up next
Yesterday
The 10 Unspoken Laws of Trust
Episode 279 of The Business Development Podcast, The 10 Unspoken Laws of Trust, dives deep into the unseen foundation behind every successful relationship, deal, and opportunity: trust. Kelly explores how trust shapes human behavior, why it’s not automatic despite being essential ... Show More
30 m
Oct 5
Startup TNT Ignites Western Canada with Tim Lynn
Episode 278 of The Business Development Podcast dives into the explosive rise of Startup TNT with co-founder Tim Lynn, a financial strategist and serial entrepreneur who has helped reshape Western Canada’s startup ecosystem. Tim shares his journey from investment banking to build ... Show More
59m 57s
Oct 1
The Underdog Power of Community
In Episode 277 of The Business Development Podcast, Kelly Kennedy takes you inside a true David vs. Goliath battle as he fights for the 2025 Signal Awards in the Business category. As the only Canadian and the only independent finalist up against billion dollar networks like Wond ... Show More
24m 17s
Recommended Episodes
Oct 2020
SDH 411: The Time to Start Your Business is Now with Kelly Roach
"The biggest thing is to start from where you are with what you've got. Do it in perfectly and have fun along the way."Meet the undisputed authority in mentoring entrepreneurs and business strategist, Kelly Roach! She transforms overworked entrepreneurs into seven-figure CEOs by ... Show More
36m 43s
Dec 2024
Sustainable Business Success
Welcome to another insightful episode of Accelerate Your Business Growth! Today, our host Diane Helbig sits down with Dr. Ian Brook, CEO and founder of Rhodes Smith Consulting, to delve into the essence of intentional transformation in the business world. In this episode, Ian hig ... Show More
41m 37s
Oct 2024
Extreme Ownership: The Ultimate Key to Entrepreneurial Growth
On this episode of the Marketing Secrets podcast, I revisit the topic of Extreme Ownership—a principle that has shaped not only my business but also how I approach every challenge that comes my way. In this return episode, I share an interaction I had with someone in our communit ... Show More
36m 4s
Nov 2024
Revolutionize Your Business in 2025 with THESE Growth Strategies
In this episode of the podcast im sharing a recent Tea with GaryVee where I dive into incredible conversations that range from tackling family business challenges to breaking free from limiting contracts and building personal brands. You’ll hear inspiring stories of entrepreneurs ... Show More
34m 17s
Sep 2024
From Basketball to Business: Dre Baldwin’s Success Secrets
In the competitive world of sales, adopting the right mindset is crucial for success. On this episode of the Sales Gravy podcast, Jeb Blount Jr. sits down with Dre Baldwin, a former professional basketball player in the NBA turned business guru to discuss why sales professionals ... Show More
49m 8s
Oct 2024
MBA2528 Q&A Wednesday: Is now a bad time to start a business?
Thinking the current economic climate might be the wrong time to start your dream business? With inflation rising and market uncertainties, it’s a question many aspiring entrepreneurs are asking. But did you know some of the most successful companies launched during tough times? ... Show More
18m 9s
Jan 2025
551: The 5 Stages of Entrepreneurship
From Self-Employed or Solopreneur through Serial Entrepreneur—what does it look like and what does it take, to go from running a one-person operation to managing a portfolio of successful businesses and creating a lasting legacy. Show Notes Page: https://www.thehowofbusiness.com/ ... Show More
23m 18s
Sep 19
MBA2679 How To Set Up a Business for Success
You’ve made a few sales, the idea’s got traction, and now you’re asking yourself what comes next. Turning a side hustle into a real business can feel overwhelming, especially when you're trying to avoid unnecessary costs or paperwork too soon. If you're ready to build something s ... Show More
19m 12s
Sep 2024
24 Steps to Launch a Start-Up
Many people aspire to entrepreneurship. But Bill Aulet, who has advised founders for decades, warns that it remains a high-risk endeavor. In this episode, he outlines concrete steps anyone can take to get a new venture off the ground — including intrapreneurs within large organiz ... Show More
28m 46s
Aug 2024
A Playbook for First-Time Founders with Nancy Twine
If you’re in the thick of building, scaling, your pivoting your business or your career: LISTEN UP! (Yes, in all caps!)This episode is for you.Today’s guest is sharing a blueprint on how to grow, pivot, and scale successfully (even if you’re literally starting from scratch.)Nancy ... Show More
44m 19s