6 Biggest Lessons From My First 5 Years of Entrepreneurship

6 Biggest Lessons From My First 5 Years of Entrepreneurship

Kelly Kennedy: Welcome to episode 295 of the Business Development Podcast, and today is very special, guys. It is my 37th birthday. It is my son's birthday and it is Capital Business Development birthday. Our five year anniversary and today I just wanna share some of the incredible entrepreneurship lessons that I have learned in my last five years in business.

And my gosh, guys, it is quite a bit. So whether you're a new entrepreneur or someone who's been in the game for a while. There is some lessons for you in this episode. You are not gonna wanna miss it.

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. In 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 Capital bd.ca.

Let's do it. Welcome to the The Business Development Podcast, and now your expert host. Kelly Kennedy.

Kelly Kennedy: Hello. Welcome to episode 295 of the Business Development Podcast. Today, guys is a very special day for me, my family, and my business. I am very excited that I get to spend it with you rock stars as well.

Today is my 37th birthday, my 37th trip around the sun. It's also my son Jett's second birthday, and it's the celebration of capital business developments fifth year in business. Yes. Three massive events on the same day. To say this is a busy week would be, uh, a total understatement. December is just a birthday Christmas bonanza.

And to look back at everything that we've been able to accomplish in just five years is absolutely incredible. I would not have believed five years ago that everything that we have done would've been possible. Think about it, guys, back in 2020, we were in the middle of COD and truthfully, it's still pretty unreal.

I can get very much caught in my head about what's next and what do we do now and you know, what is the next opportunity, the next thing to do. It's easy to do that. It's much harder to sit back and reflect, and so I get one day here every year that kind of forces me to reflect, and this one, especially being the five year anniversary.

I'm gonna dig a little bit deeper today. I thought it would be fun to reflect on the last five years with you and let you in on some of the takeaways and lessons that I've learned along the way to help you all on your individual and business journeys. Obviously I can't hit on every single lesson. I've just touched on here six lessons that I think ultimately are very powerful for you, and you probably will be surprised they may or may not be the typical Kelly Kennedy advice.

It's not all upside. I think today we might be talking about some of the, uh, the challenges of entrepreneurship, but. As you all know, there is always a way forward and we are going to get there together. So let's just get into it. Number one, entrepreneurship is scary. Full stop. Entrepreneurship is scary.

I'm not going to sugarcoat it for you. If you are jumping in, you know that and you don't need anybody else to tell you any differently. For many of us, it's the very first time that we have really had to bet on ourselves, and I mean really like 150% throughout the show. I've had many entrepreneurs tell me that they had to burn all the bridges, put themselves in a sink or swim situation.

The fear for the jump was so high, it was the only way that they could do it. The fear that you have when you start never really goes away, and I think you might find that surprising. It transforms. That's what happens. Your fear transforms and subsides over time. Entrepreneurship does not get less scary.

Instead, you get better at trusting your own ability to handle what comes at you. With Grace, you learn that you can bet on yourself because you have to bet on yourself over and over again. But the cool thing is, like anything in imposter syndrome, the more often you bet on yourself and win eventually.

Your brain has no choice but to accept that, heck, you can do stuff. Not only can you do stuff, you can win. You can actually win, and the more often that you bet on yourself and win, bet on yourself and win. Eventually it gets less scary. You get better at trusting yourself. Now, here's the thing. Learning that you can bet on yourself is probably the greatest gift that entrepreneurship has for you.

It's not the money, it's not the prestige, it's not, you know, all of the amazing things you do for your clients. It's being able to bet on yourself 100% and trust yourself 100%. That in my mind, if I look at the past five years. That is the greatest gift that I've been given through entrepreneurship. Number two, version one of your company.

Will suck. Lemme repeat that version one of your company will suck and it's totally okay. It's totally okay. When I started Capital Business Development, I thought I had it all figured out. I wrote my business plan, and while I did have some early successes, it did not take long to realize that I had nearly none of the answers.

I did not have it all figured out. Here's the problem. When many of us start businesses, we are still thinking like employees. We are coming from the employee world. You've maybe worked for 20 years, 15 years, 40 years as an employee. That wiring doesn't just go away. And the funny thing is the wiring. As an entrepreneur, it has to change.

We are still thinking hourly. We are not committing 100% to what we need to do. We are not yet open to accepting the changes that we really need to make both personally and professionally. And don't get me wrong, there will be changes required on both sides before we are able to truly succeed. See the person that you were, got you to, entrepreneurship and that person is amazing, the entrepreneur that you are today, if you are a new entrepreneur.

Everything that you've learned has gotten you here, and that's amazing. And that's not to be discounted, but you have to remember that the person who got you to entrepreneurship is not going to be the same person that will make you successful at it. You are going to have to grow into the person who is going to make you successful at entrepreneurship.

And yes, that means personal and professional changes and um, it takes time guys. There's no two ways about it. The only way that you get there is by going through it. Taking on the struggles, figuring out where you're deficient, figuring out where you need to learn, and accepting that you don't have all the answers.

The sooner that you can accept as an entrepreneur that you don't have all the answers, the faster you are going to evolve. Because if we can accept we don't have all the answers, we can be willing to go and find them. And the moment we start doing that. Asking for help, figuring out what we need to know.

That is the superpower that is going to get you to the entrepreneur you need to be. See. If I look at capital business development over the last five years, my company has shifted significantly from my initial plans. And it continues to evolve every six months, guys, not even every year, like every six months.

It changes all the time. And your ability to adapt and learn and try new things is what will make your company successful. Never stop trying new things and never stop learning. Guys, no matter what you do, you're only an expert until yesterday. Tomorrow is a brand new day. Be humble. Be willing to eat humble pie.

Be willing to say, I don't have all the answers, but I sure as heck am willing to find out. That is the secret sauce of every exceptional entrepreneur that you know, they don't have all the answers, and it's okay because they can figure it out. Number three, the only thing consistent in your business will be change.

The only thing consistent in your business over time will be change. I used to hate change, guys. I hated it. I advocated against it significantly. If I look at like the wins I had as an employer, or things I thought was wins, it was pushing back against change. Change never seemed good to me and it always screwed with my routine.

I think that was the problem. It's like as an employee, I had this like routine and it's like, I wanna do what I wanna do and I just wanna be able to go to work, do the thing, go home that is not going to serve you as an entrepreneur. I had to flip the script on myself once I realized that the secret to long-term success for any business is to accept.

That change is inevitable. No matter what service you have today, if it never changes, it is going to become obsolete. The thing is, the world is shifting around you. Even if you choose to not accept the change, and that's fine. You can make that choice, but understand the world is not going to choose that.

The world is not going to choose. No change. It's going to continue to change endlessly. And if you look at the only thing that's consistent in this world, in business, it is the fact that time and change is going to keep moving forward. The secret to long-term success for any business is to accept that change is inevitable, and once you accept that change is going to happen with or without you.

You can learn to stop fearing it and start embracing it instead, guys, I was afraid of change. I was pushing back against change because change always seemed bad as an employee. It seemed like, oh my gosh, if some things change, I'm gonna become obsolete, or I'm not gonna matter anymore. That simply might've been true in certain situations as employees.

However, it does not serve you as a business owner. It does not serve you when you have to keep evolving your services, your products, to meet an ever changing market. Okay. The reality is it doesn't matter whether you're Ford, Microsoft, Amazon, every company on Earth, the only thing consistent for them is going to be change.

If you look at Apple, the reason that Apple has always been so successful is that they were not afraid to make their own products obsolete. If you look at the iPod, and I talked about this in a previous episode, if you looked at the iPod, they absolutely decimated the iPod market when they released the iPhone, and they did it intentionally.

Why? Because if they didn't do it, somebody else would. If they didn't release the iPhone, it wouldn't be long until Samsung or some other competitor, Blackberry maybe was going to do it, and they knew that it was going to mean billions of dollars in lost sales from the iPod. But they did it anyway because they recognized that if they wanted to stay market leaders, they had to embrace change no matter what it costs them.

All the top companies in the world, guys from forward to Apple, to Amazon, to Microsoft, to nvidia, they all embrace change and it has allowed them to compete year over year over year. The faster that you can accept changes necessary, the faster you will move forward. Don't be afraid to destroy your own products in the name of change, because if you don't do it somebody else will.

Number four. Your three, five and 10 year plans are going to fall apart, totally fall apart, and that is completely okay. The only thing that you can bank on is change. We've talked about that the world is evolving around us and at a speed that none of us can really plan for. At the moment, even the best companies on earth, guys are struggling at this point with their five and 10 year plans.

Five years ago when I started Capital. I had not even been aware of AI guys. It had never come across my plate. It had never come up in any discussions, aside from maybe some discussions I had with some friends in high school who were like, Terminator would be crazy. That was my, that was my understanding of ai and I'm sure a lot of you feel the same way.

I was like two years into capital business development. Nearly six months or so into the business development podcast. The very first time I even played with chat GPT, yes, I was a little bit behind, but either way, it wasn't even on the radar. I was still putting like 30,000 kilometers a year driving my truck around and dropping brochures in business cards.

Like I was still doing bd, the old school way. COVID was like just getting rolling. When I started the company, nobody knew what that meant. Nobody knew how the world was going to change. And uh, boy did it change. Today I do 99% of my business development from home guys, like 99%. I have multiple supercomputer AI's that all of us have access to that we definitely didn't have access to five years ago.

I speak to the world through this show. I coach internationally through my coaching programs, and I'm building a leadership community for leaders by leaders, and frankly, it's because the world has changed. All of this stuff became available. None of it could have been planned for guys. None of it could have been foreseen.

The best opportunities you will never see coming your five and 10 year plans can't see that coming. 'cause honestly, you can't see two years from now, let alone five the. Definitely let alone 10. Now, like I said, my crystal ball showed me none of this, like absolutely none of this. Guys, I could not have planned any of this.

I just kept moving forward. I kept providing my services and I kept talking to people and figuring out what they were looking for, what challenges were coming up, and watching other creators and other people that I know and respect and seeing what they were doing. And as the opportunity showed up some of them, so obviously that I couldn't say no.

Like the Business development podcast, I said yes, I jumped in with both feet. No, I didn't have all the answers when I started this show. Guys, I'd never even picked up a mic before. I definitely hadn't ever edited audio. Everything here was learned, but I was willing to learn. I was willing to try it. I was willing to figure it out.

And here we are, nearly 300 episodes later, nearly three years later, and we are still improving and working on this show year over year because I don't have all the answers. And as better things show up, and as I talk to more people. It will become obvious. You don't have to have all the answers. You just have to be in the game and be willing to say yes when those opportunities inevitably show up on your doorstep.

Plans are great guys, but expect the unexpected, the best opportunities you will never see coming. Number five, entrepreneurship is a roller coaster, like, and this is super, super real. Okay? This ride has ups and downs, and the ups are exceptional. You feel like you're going to the moon and the lows can make you question everything you've ever done in your life.

Okay? Nothing goes up forever, which means that when it's good, enjoy it because it's going to eventually turn around and go down. Okay? But you have to remember even on the dips, even when things are not going great and it feels like the world is against you. Every dip comes to an end as well. It is a rollercoaster, ups and downs and ups and downs.

If you're high, eventually you're gonna become low again, and if you're low, no matter how crappy and ugly and shitty, it looks like the world is gonna end and your company's gonna fold. Something's gonna happen, and you're gonna be right back on that upswing again for the most part and be like, holy crap.

Oh, thank God that's over. But it happens. That is literally entrepreneurship and sometimes that all happens in one day. That's the craziness of it all in the hard times. Like I said, the world feels like it's coming down on you. And don't be afraid to take a knee. I've done it many, many times. I talked about this on a past episode, like not even that long ago.

Don't be afraid to hop on one knee and ask your higher power or your belief system for help. There have been multiple times on this journey that it felt like hope was lost and this whole thing was gonna come crashing down, and then when you least expect it, the universe, God, whatever you believe in, picks you right back up, puts an opportunity in your lap and pulls you right back on your feet and says, not yet in the hard times.

Take a minute to reconnect with your why and remember. You got this far and you can get yourself out. Whether you believe you can or you believe you can't, you are right. Remember that no matter what the situation, if you believe you can get yourself out, you can get yourself out. And if you believe all hope is lost, then all hope is lost.

Number six, community is everything. Nothing that I have succeeded at was done completely on my own. And I actually had to question this 'cause I got questioned by Andrew Z. Brown, the get referred guy who was like, who? Who kind of put me on the spot and said, Kelly, look at the best contracts you ever got.

Did you really get those completely on your own? And I hated to say it, the answer was no. People vouched for me. People stood up for me and said, you gotta meet this guy. He's doing stuff. You gotta meet Kelly. He can help you with your business. The best contracts I've ever closed came through community, came through.

People vouching for me, people who believed in me, people that I knew. And it doesn't matter guys, whether it was my retainer, contracts to this podcast, to my coaching, or even now, the Catalyst Club. It's other people. It's the word of other people that keeps these things going, that keeps your world changing, your world growing.

We are the sum total of the great people that we surround ourselves with, and I'm not sure that I believe that in the beginning of my entrepreneurial journey, but I can tell you without question, I believe that now we are the sum total of the community that we surround ourselves with from our friends to our family.

To our peers, to our coworkers, to our mentors. We are the sum total of the people that we surround ourselves with. It really does matter. Community truly does matter. Your community will either lift you up or tear you down. I have been blessed with meeting some absolutely incredible individuals along my journey so far, and I think the thing that most entrepreneurs are actually missing at this point.

Community. Somewhere along the way we got told we had to do it on our own. We got told that it all relied on us, that everybody was relying on us and all the pressure was on our shoulders. And what I've realized was, yes, we all have a lot of pressure on our shoulders as leaders, but guess what? You can ask for help.

You can find a community to support you. You can find a safe space to do that with peers who get it. If you look at what's going to change here in 2026, I think that 2026 is going to be the year that we all find community again, I think it's gonna be the year of community. I'm making my prediction right now.

Every chance you get to build your circle, take it. It will help you. It will help other people, and it will make you better. And last but not least, your bonus lesson above everything else. Everything else, guys. Believe in yourself. You absolutely can do more than you ever imagined. Rome was not built in a day and neither is your business.

You just take one little step, then another. Every time you take a step, the next step will be revealed. The next thing that will make sense for you will be revealed. You just have to keep going. We overestimate what we can do in one year and we underestimate what we can do in five. I've been told that this entire journey and, well, I'm at year five guys, and I can tell you that is absolutely correct.

I could not have planned all the stuff that we've been able to do in five years. From Capital Business Development to the Catalyst Club, to The Business Development Podcast, to Authentic Hustle to Business Development Mastery like. All of this stuff is just blows my mind that we were able to do all of this in five years and it makes me just be like, what is coming in 10?

'cause it's gonna be exceptional. But none of it was in the plans guys in year one. I could have never seen all of the stuff that we would be able to do in five short years. You can do that too. Keep going everyone. If I can do it. So can you, and last but not least, if you are heading into 2026 and you do not have a community yet to support you, and you are a leader out there of some type or another, I want you with us.

I want you with us, I want you to consider joining The Catalyst Club. The Catalyst Club is a completely. Online community, we do four to five live events each month. You can attend them from your phone, from your laptop, from anywhere in the world, and you can surround yourself with some of the most exceptional leaders out there in a place where people actually understand what you are going through.

Leaders need other leaders. Leaders need support from other leaders, and that is what we are building a community of support. Four leaders buy leaders, and I want you to join us. It's just $29 a month, and you can join at www.kellykennedyofficial.com/TheCatalystClub. Shout outs this week. Colin Harms, Rodney Lover. Jillian Schecher, Trish Greaney, Salvatore Manzi, Ruthann Weeks, Daniel Monson, Benjamin Johnson, Ricco Baffa, Gary Noseworthy, Andrew Z. Brown, Pamela Staples, Steven Langer, Jamie Bigger, Barry Hartman, David Citron, Rachel Blanton, Randy Lennon, Chris Friesen, Irene Lay, Shawna Devlin, Jay Sanderson, Tatsiana Zametalina, and Susan Poseika.

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.