Choosing Entrepreneurship Changed Everything


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.
Choosing Entrepreneurship Changed Everything
Kelly Kennedy: Welcome to episode 239 of the Business Development Podcast, and today's show is for my rockstar entrepreneurs. I'm sharing the biggest lessons I've learned on my journey through entrepreneurship, why I chose to build my own path and how it stacks up against traditional employment. This is for those ready to take action and build something incredible.
Stick with us. You're not gonna wanna miss this episode.
Intro: The Great Mark Cuban once said, business happens over years and years. Value is measured in the total upside of a business relationship, not. By how much you squeezed out in any one deal and we couldn't agree more. This is the Business Development podcast based in Edmonton, Alberta, Canada, and broadcasting to the world.
You'll get expert business development advice, tips, and experiences, and you'll hear interviews with business owners, CEOs. And business development reps. You'll get actionable advice on how to grow business, brought to you by Capital Business Development CapitalBD.ca. Let's do it. Welcome to The Business Development Podcast, and now your expert host, Kelly Kennedy.
Kelly Kennedy: Hello. Welcome to episode 239 of the Business Development Podcast. And I know I say it a lot guys, but my gosh, 239 episodes of the show. Still to this day, can't believe it. And I think it's a fitting one because today I wanted to chat all about lessons in entrepreneurship. So while we're not gonna talk much about the podcast, it's definitely been been spurred out of my entrepreneurship passion and kind of the path that I journey down.
So it's still one of those things that every once in a while just blows my mind that we've come so far in such a short period of time. We're around two and a half years. Into the Business Development podcast and to be at 239 episodes. It's an honor and a privilege. Thank you. Thank you. Thank you so much.
Today I wanted to speak to my lessons learned so far in entrepreneurship, my views on it versus employment, and provide you with some tips to consider for starting your own businesses here in 2025 and beyond. But before we do that, we have to go back. Way back. It was a cold December day, December 3rd, 2020 when I incorporated capital business development.
Little did I know that just four and a half short years later, I would have an industry leading podcast. I would've released hundreds of episodes and made a lasting impact on the business development community worldwide. Just one week before I had been pulled into the boardroom with a president of a company that I had helped build from the ground up over the previous 10 years, and I was given the news, Kelly, this Covid thing, it's hitting us really hard and I don't know what the next few months look like, let alone the next year.
Do you have a plan If this does not work out?
That was, that amount sums up how I was feeling in that moment. If any of you were wondering it it really in that moment felt like my whole world had just blown to pieces. The news hit me like a ton of bricks. I thought about doing my own thing many times. I even had a great business name idea.
Capital Business Development. Why? Because I lived in the Capital City of Alberta and capitals exist everywhere, so why not? It seemed like a cool and even premium idea, but after working for 10 years as an employee, I. Vacation time, benefits, bonuses, financial obligations of life, and obviously my status of being a long time employee and a key employee in the organization.
The jump to entrepreneurship was more of a thing to dream about than a reality. Yeah, I had the ideas forever, guys. The reality is I was thinking about how I could make a massive impact in the business development world, probably five years into my career, where I realized that there was a lot to do here.
It was a wide open space and needed a lot of help. I knew this early, early on, but employment had me, that was right up until this moment, and in this moment, I knew. My boss was not joking, as he had many times before. He was dead serious. This was not a drill. The world had completely shut down, and the company that I had worked so hard to build a career in was in serious trouble.
A week later on my 32nd birthday, Capital Business Development was born. Little did I know at that moment that my incredible journey was just beginning. As it turns out, the path to entrepreneurship is not always paved in gold. I think a lot of the time we need a catalyst, a moment where life literally pulls the rug out from under you and forces you to consider what is next or what could be next.
In retrospect. This opportunity was the biggest opportunity that life had ever handed me to become the best version of myself and realize my true potential. But in that moment, I felt like a piece of me, an identity that I had worn since college and maybe even before that had died. And while that was the case, in some ways.
The truth was that an opportunity of a lifetime was truly just beginning. I hope that I've found at least one of you out there today who has found yourself stuck between a job and a vision. Maybe you just had the hard talk in the boardroom that I talked about a minute ago and found this episode. If so, I hope that you find the clarity in this episode to do something incredible.
I know some of you might be asking right now. Kelly, you spent 10 years at an organization. It didn't quite go to plan. Covid came up, things were shifting. Why didn't you just go and get another employment position? And so I think in order to continue this story, we have to really dive deep into some of the reasons why I chose entrepreneurship.
Like I'd mentioned earlier in the story, it wasn't the first time I dreamed about it. It wasn't the first time I'd actually sat down plenty of times and like I said, came up with plans, came up with an idea for a company named that company. Literally wanted to do it guys, but I just wasn't ready to take that leap.
I had a great job. I worked at a great company. I had a good position. I got paid well enough. It did well enough to forget my dreams for a little while. I just wasn't quite ready to take that leap at that time. But here are some reasons why I chose entrepreneurship in the first place. Okay, why did I take that leap?
Number one, I wanted to earn what I was worth. I could offer exponential value to my cost at this point in my career. And I had worked through three recessions, the great recession of 2008. The oil and gas downturn in Canada of 2015 and now the 2020 Covid Global Pandemic. I was working my ass off as are many of you, and still falling behind, and I know many of you are feeling that way right now.
In this moment, I wanted more and I was done waiting for somebody to give it to me. Number two, I wanted freedom. If you've been listening to the show for any length of time, you guys know that freedom is one of my top priorities in life. I wanted freedom in every way that I could get it. I wanted financial freedom, the freedom of time, freedom of creativity, freedom of location, and freedom of purpose.
Freedom was absolutely critical in my desire to become an entrepreneur. Number three, I wanted safety. Employment was not protecting me or my interests. The 30 year career and gold watch that I'd been sold by my parents' generation was about as dead as the dinosaurs. And I had finally realized that if I wanted safety.
I needed to find it somewhere else. Number four, I wanted to change my industry business development for the better. I had the process and skills that could help thousands of businesses grow. I knew that I could make a bigger impact working fractionally, bringing high level strategy to companies that needed it most.
I knew that if I wanted to make an impact, I was never gonna make it in the way I wanted to as an employee. Number five. I wanted to prove to myself that I could do it. It was time to see what I was made of. I'd built other people's companies. I wanted to see if I could do it for myself. In the two and a half years since I've launched the business development podcast, I've probably spoken with hundreds of entrepreneurs in various stages of launch, whether it's still an idea stage, whether they've incorporated, but they haven't taken the leap yet, whether they're working two jobs and they're just waiting until they can make the full leap into entrepreneurship on their own.
Or maybe they've just launched their company and they were looking for advice. But I find the same thing comes up over and over again. The illusion of Safety in employment. Okay. We've been sold a bill of goods. Okay? We've been sold a bill of goods with employment and that was that our parents' generation could go get a great job, work an entire career there, maybe 30 years.
My dad is a great example of this. Retire, get handed a gold watch and a pension and a retirement plan and be able to just live a good life. That is long, long gone. The safety myth was this, get a good job with a strong company and make it to retirement. Same company 30 years. Maybe once, but that ship has long sailed people.
Employment feels safe right up until it isn't. Layoffs, ceilings, burnout, and it's happening more than ever. Entrepreneurship feels risky until you build stability through systems, relationship, and control. The key difference is this, in employment, someone else sets the ceiling in entrepreneurship. You do.
That is powerful people. I have been an entrepreneur for nearly five years at this point. It has been an incredible journey so far, and here are some of the truths that I've learned along the way. Entrepreneurship is on you for at least the first year and possibly many. If you choose to be a solopreneur.
You are the engine. You must build momentum. Whether you win, whether you lose, it's up to you. It's up to you on how much time you're gonna put in, how much effort, how much you care. But if you are willing to put in the time and the effort and the consistency, you are gonna stack the odds in your favor.
Number two, everything takes longer than you plan. Give yourself grace. It's okay. It's okay. Entrepreneurship is a journey. It's a marathon, not a sprint. Number three, you overestimate what you can do in a year and you way underestimate what you can do in five. Think about it this way guys. I changed an industry in five years.
I think you can beat it. Number four, work-life balance is a total lie. And guys, I've interviewed enough entrepreneurs at this point to tell you that is absolutely true work-life balance doesn't exist over 160 interviews. To confirm that over and over again, when people tell you achieve work-life balance, it's probably not going to happen.
As an entrepreneur, you might be able to earn it. But it's down the line. It is not immediate. It's gonna take you time to earn balance, but I think over time it can be earned. Be prepared to work harder than you ever have, but also be prepared to feel more rewarded by your work than you ever have as well.
Number five, work will feel rewarding more often. Here's the thing, as an entrepreneur, work is probably the most rewarding it will ever be. Why? It's your baby. It's your effort. It's your life on the line. It's your reputation on the line. It's your business on the line. You're gonna care more. You're gonna put more effort into it.
You're gonna do a better job, and you're gonna love being an entrepreneur, likely more than you ever could have. Being an employee, you likely will be even more driven than you have ever been in your life. Number six, insurance bills suck, but make them a non-negotiable. You absolutely need insurance, and it doesn't matter what you do, whether you're a contractor, whether you're providing services, whether you talk on a podcast, or whether you give advice, make sure that you have appropriate insurances in place to cover your ass because you never know when you might need it.
Number seven. Expenses pile up fast. Okay? Really fast. Expenses are crazy. Keep a handle on them. Your cashflow is absolutely king. You have to make sure that you have more money coming in than is going out as often as humanly possible. Make sure that you're keeping an eye on all of your recurring expenses that come up once a year, once a month, whatever it is, and review your credit cards often.
Okay? It's easy. To be paying for things and miss it very easy, easier than it ever has been. Check your subscriptions regularly. Review your credit card bills regularly, and at least once a year do a full audit on your subscriptions to make sure you're only paying for what you are using Number eight.
Your brand is louder than your mouth. It's what people say about you when you're not in the room that matters. Okay? That is what a brand really is. It's not what you say it is. It's what other people say it is. Okay? It's important that you are leaving a good reputation everywhere you go, that you're doing the best work you can, that you're providing the best products and services you can.
Always, and that you're getting those reviews, that you're getting that feedback, that you're making sure you're constantly improving and the people you serve are getting value. Okay? If you're doing these things right, your business will make it. Number nine, find ways to use your skills and talents to give back.
I found my passion for coaching by giving my knowledge away on the Business Development Podcast. I didn't realize how much I would love teaching guys. Obviously, I was in business development. My job was to find new business. What I learned later is what I really love to do is teach other people the skills of business development, the skills of entrepreneurship, the skills of podcasting.
These are super fun, and teaching people is a great time. I would've never learned that without giving my knowledge away on the podcast. So don't be afraid to give back. Don't be afraid to donate some of your time to make an impact. Number 10, tomorrow is a brand new day. Listen, I don't care who you are. I don't care what you're an expert in.
You're only an expert until yesterday. Okay? Tomorrow is a brand new day, especially with the advent of AI people. The world is changing. It's changing rapidly. The world we live in right now in 2025 is gonna be vastly different by 2029. That's how fast things are evolving. Make sure that you never stop learning and never stop pushing your boundaries and finding more efficient ways to do what you do, because if you don't figure it out.
Somebody else will. Number 11, consistency wins always, not talent, not passion, not motivation. Consistency over time breeds success. I've been saying that from the very beginning of this show. What has made me powerful in business development is consistency. It's repetitive tasks, and getting really great at doing them, even when I don't feel like doing them, maybe especially when I don't feel like doing them.
Consistency over time is king. Number 12, iterate, iterate and iterate some more. Failure is fine. Just fail forward. Okay. The reality is version one of capital business development sucked. It sucked. It needed to fail. I didn't understand how to do my packages right. All I knew as an employee was that I need to charge some money for my services, right?
Iteration one of any business, you start. It's pretty unlikely it's gonna be the final version, like extremely unlikely. Think about like Ford, right? Ford started making what? The Model T. Yeah. Now they make the Mustang. Now they make the Ford gt. The reality is that car wouldn't make it today.
The cars they have today are pretty frigging incredible, aren't they? Think about it from the standpoint of version one of your business is a bicycle and you need to get it to a Ferrari. You're gonna have to fail at the bicycle to eventually get it to the Ferrari. So don't worry about it. Failure is fine.
Fail forward. Number 13. You are capable of more than you could ever imagine. Listen, whatever you do, wherever you came from, whatever your history. You can do something incredible. You can change the world. If I can change the business development industry from my house through a podcast, you can change the world in your own major way.
It's just a matter of time. The secret is you just have to take that first step, have a vision and execute. Number 14, the best things you won't see coming. Listen, the best relationships that have come into my life, the best sponsors. The best opportunities, the best clients. I could have. Never seen them coming.
I wasn't shopping for them. They found me. Those opportunities came to me. Listen, almost everything that I've planned and tried to execute it didn't go to plan. It went in a completely different way, but the way that it went was better than I could have ever imagined. Be okay with the fact that the best things you won't see coming, you just have to be ready to say yes when they show up at your door.
Number 15, the universe has an incredible plan for you. Have faith. Have faith. I don't care where you're at today. I don't care if you're having your worst day, the best day, or somewhere in the middle. The universe has an incredible plan for you. Whether it's God, the universe, whatever you want to call it, your time is coming.
An incredible thing is coming to your door right now. Have faith. Have faith be ready to say yes now. Hopefully, if you've heard all of the show today, you might be thinking about starting your own business. Okay. If this is you, if I got you today and you're like, okay, Kelly, I get it. I'm inspired, I'm excited.
I wanna do this. Here are some tips for launching your business. Number one, start before you are ready. It will never feel like the right time. Take it from me. I told you, 10 years in employment. Probably had the plan to go to my own for five years. It never felt like the right time. It took a catastrophe.
It took me losing that position for me to be like, okay, I'm ready. I'm gonna do this. It's never gonna feel like the right time. It's always gonna feel stressful. It's always gonna feel like a hard decision. Just understand that. Number two, I. Validate fast. Talk to your customers early. If you have a product or service, whatever it is, just call some places and ask them if it's something they'd be interested in.
Feel free to talk to them. Say, I haven't launched my service yet, or I haven't launched this product yet, but is this something you would be interested in? Run them through it. Ask. Test your product. Test your service before perfecting it. It's okay. Like I said, V one's gonna be a bicycle. You gotta get it to a Ferrari.
It's gonna take time, it's gonna take iterations. It's gonna take lots and lots of conversations with people who need your products and services. Don't be afraid to have those conversations and don't skip this. Step number three, build a brand, not a logo, a voice, a reputation, a feeling. Okay.
That's what a business really is. That's what a personal brand and a business brand is all about. It's not a logo. It's not a logo. It's a voice, a reputation, and a feeling. Number four, know your numbers. How much money do you need? Don't just survive, thrive, and grow. Listen, you probably need to make at least double what you think you need to make.
That's the hard truth. Entrepreneurship is super frigging expensive running your own business. It never ceases to amaze me how much money I have to earn just to get by. Okay. You have to make a lot of money as an entrepreneur. Understand your costs, understand your expenses, and understand what you need to charge to make sure that they're not just covered, but you're making a profit.
Know your numbers. And last but not least, number five, surround yourself with builders. Your circle defines your ceiling and this is absolutely true. Entrepreneurship isn't easy, but it's worth it. You trade certainty for possibility, comfort for growth, and a paycheck for potential. But in return, you gain freedom, purpose, and the power to build something that is yours.
If you're sitting on the edge waiting for the right time. Hear this. It won't come. You create the right time by moving, so take the leap back yourself and start building the life and business you have always dreamed of. I hope that if you're hearing this today and you're on the fence about launching your own business, maybe it's been an idea for a while.
Maybe it's all out on paper. Maybe you're in a job or a career that is sucking the life from you and you just want to do something different. Let this episode be the catalyst. Let this be the kick in the ass, the boardroom talk, the firing, whatever it is, the Covid crash. That kicks you into high gear.
Take action today. Whatever it is, even if it's small, take action, I think you'll find in no time entrepreneurship will be calling. And if this message resonated with you and you're ready to take the next step in your business development journey. I'd love to support you. Whether you want hands-on coaching inside of the Business Development Mastery Accelerator, or you're looking to plug into a powerful network of builders and leaders inside the newly created Catalyst Club, we've built the space for you.
Visit KellyKennedyOfficial.com to learn more and join us. Shout outs this week. Colin Harms, Alinnette Casiano, Kathryn V., Cruz, Gamboa, Nadir Ali, Oliver Ramirez, Andrew Z. Brown, Kelsey Watt, Gary Noseworthy, Danielle Forcade, Jamar Jones, Steve Austin, Sherri Allen, Eric Portillo. Paul Walsh, Vijayan Swaminathan, Thomas Stenson.
Jeffrey Agyepong, Iza Montalvo, John Pelley, Adam Kimmel, Michael Steeves, Chris Steffens, Kim Jurina , Dr. Elise Victor, Jack Dyer, Shannon Smith and Rodney Lover. Until next time, you've been listening to the Business Development Podcast and we will catch you. On the flip side,
Outro: this has been the Business Development Podcast with Kelly Kennedy.
Kelly has 15 years in sales and business development experience within the Alberta oil and gas industry, and founded his own business development firm in 2020. His passion and his specialization is in customer relationship generation and business development. The show is brought to you by. Capital Business Development, your business development specialists.
For more, we invite you to the website @ www.capitalbd.ca. See you next time on the Business Development Podcast.