Overcoming Challenges and Embracing Failure in Entrepreneurship with Kerry-Ann Powell

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Show Notes:

If you’re going to hell, just keep going. This good old saying applies to business too. Our guest today has some tips down her sleeve to help you always stay the course.

Meet Kerry-Ann Powell. Kerry-Ann is the Founder and CEO of Trafalgar Strategies LLC, a business strategy firm working with small and medium-sized companies. With her experience of over 20 years as a Washington, DC attorney, lobbyist, and high-level fundraiser, Kerry-Ann helps businesses thrive in business and in life. She’s an expert on strategic consulting, executive coaching, and leadership development. After raising $120 million to build the Martin Luther King Jr. memorial, she decided to dive into entrepreneurship and launch her own strategic business and consulting firm. Over the years, Kerry-Ann has collaborated with many international brands, organizations, and institutions, such as Working Women’s Magazine, Dallas Leadership Foundation, Philanthropist Russell Simmons’ Rush Philanthropic Arts Foundation, and more.

She believes that entrepreneurship doesn’t have to be chaotic. With the right strategy and vision, you can run your business smoothly and effectively.

In this episode of the Think Business with Tyler podcast, we talk about the challenges of entrepreneurship, the importance of scaling at your own pace, how to align your business vision with your life plan, and how to keep going even during tough times.

If you want to get some valuable insights about entrepreneurship, make sure you tune into this episode to hear what Kerry-Ann says.


💡 Name: Kerry-Ann Powell

💡 What she does: She’s the Founder and CEO of Trafalgar Strategies LLC, a business strategy firm working with small and medium-sized companies.

💡 Noteworthy: Kerry-Ann is a global business strategist, speaker, and champion of small and medium-sized businesses. She has over 20 years of varied experience a Washington, DC attorney, lobbyist, and fundraiser positions.

💡 Key Quote: “I do believe that a business is like nature. So if it’s not growing, it is kind of dying.”

💡 Where to find Kerry-Ann: LinkedIn

Key Insights

Challenges are a natural part of entrepreneurship. Building a business from scratch is never smooth sailing. There are always going to be ups and downs while you’re trying to scale and grow. So, if you’re afraid of failure, try to change your mindset. Embrace failure and accept it because challenges are an inevitable part of entrepreneurship.

Kerry-Ann explains, “I remember sitting down there thinking, wait a minute, I’m questioning my own ability, questioning my own capacity to run a large company, questioning all these things. And so I did hit a wall, and I must admit I shrunk in and spent a couple of weeks just kind of feeling a bit sorry for myself. Like I can’t do this, you know? But I think it was such a great thing for me because it helped me sort of realize this is how business is. There are some things that must happen in order for scale.”

Scale at your pace. Every business is unique, and so is yours. How you scale and grow your business might differ from what everyone else is doing. The key is to ask yourself what you want from your business and how you want to achieve it.

Kerry-Ann says, “You don’t want to grow and grow and scale and scale, and then you are just so burnout out, you have no creative energy for the next thing. Entrepreneurship is about building and growing, and creating new ideas, and putting them into place. And if you get to that point where you’re like, ‘No, I just want to sit around and drink mimosas…’ Obviously, there’s vacation, there’s downtime, but right now she’s just like, ‘I’m just done’ because that’s called burnout.”

Your business vision should fit into your life plan. When starting a new business, it’s vital to first understand what your vision for the future is. And not just business-wise but in terms of your personal life plan. Make sure your business fits into your life plan.

Kerry-Ann explains, “How do you see life going for you? What do you want it to look like? And then being able to look at the business vision and see how it fits into how you see your life going because if the vision of the business doesn’t fit into your life plan, that’s the first challenge we have in building, in scaling because you don’t know really what you want it to look like.”

Just keep going. Tough times are inevitable in both life and business. But that doesn’t mean you should quit. Quite the contrary. Allow yourself to have a few dark moments, but always get back up.

Kerry-Ann says, “Today may be dark, and you may not want to even pick up that pen or get on that computer. Today’s not that day, but tomorrow do something small towards that. Also, action breeds momentum. It’s like if you’re sitting in the dark spaces and you’re in the valley of despair, thinking about it isn’t going to get you there. You have to just do something, make one step. So that’s my tip. Just don’t quit.”

Top Quotes

“If I’m looking at my calendar and the different roles that I play, one of which obviously is caretaker of me, is kind of not scheduled in, then I’m going to make sure that I put that in there. […] ”

“There is a falsity that’s out there, and it’s not serving anyone because it’s giving people a different idea of what it means to really grow a business and a business that’s going to last.”

“The thing is, people are like, ‘Oh, well, that’s a failure.’ No, it’s not failure. It is what growing a business looks like, and I think the best lessons we learn are the ones that kind of hurt a little bit because then it’s ingrained in us, and we’re like, okay, not doing that again.”

“I think for the most part one, I really believe that the owner and the folks that are in the inner circle of what that business looks like, the founder, the co-founder of those kind things need to determine what scale looks like for them.”

“The thing about human beings and entrepreneurs generally is that they’re going to get bored at some point. They get to a point where it’s like, ‘Okay, I’ve done this. What’s the next thing?’ So if you are in that place, I think this is when there’s a need to sort of say, ‘Okay, what is the strategic objective for the business for the next five years?’ And that’s where you can start creating some strategic objectives and kind of putting some really beautiful things into place.”

“Strategy comes from the gut, from the belly of the beast. It’s like, who do we see our business as today? Who are we serving today, and where do we want it to go tomorrow? That’s really all strategy is, and then in between that, we say, how do we want to do it?”

“I like to think of it as one coin. I call it inspired leadership, on the other side of the coin is a rockstar team. If you are an inspired leader, then you’re more than likely to foster a rockstar team. Here are the principles, though, that will make that work. I look at leadership as sort of three things. How you lead yourself, how you lead your team, and how you lead your organization.”


Trafalgar Strategies Website

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