How to Start a Business When You Are Scared: The Fear and Mindset Shifts That Make the Difference
The fear of starting a business is real — but it does not have to be a permanent barrier. In this episode, Scott Dillingham shares the exact mindset shifts and practical first steps that helped him push through fear, build momentum, and create a business that has helped thousands…
The fear of starting a business is real — but it does not have to be a permanent barrier. In this episode, Scott Dillingham shares the exact mindset shifts and practical first steps that helped him push through fear, build momentum, and create a business that has helped thousands of Canadians.
Scott discusses embracing risk from real estate investing, viewing setbacks as learning opportunities—like potholes to navigate—and urges listeners to "just do it" to overcome fear.
He emphasizes mindset: Write down goals affirmatively, visualize success as already achieved, break big goals into small steps for accomplishment, and focus on strengths over weaknesses via feedback from others.
Maintain positivity by reframing negative thoughts, surrounding yourself with uplifting people, and dedicating time to self-improvement through books, courses, or seminars—avoiding negativity that hinders growth.
Delegate weaknesses (e.g., hiring an operations manager) to work on the business, not in it; success stems from persistence, ethical practices, and viewing failures as temporary.
In 2025, Canada's small business landscape sees AI adoption, sustainability focus, e-commerce growth amid improving inflation, but challenges like trade deficits and costs—favoring resilient startups in tech services, green energy, and freelancing, per BDC, Shopify, and CMHC reports.
This episode motivates entrepreneurs with practical mindset shifts for success in 2025's evolving economy.
Guest Bio
Scott Dillingham is the host of The Wisdom, Lifestyle, Money Show and founder of LendCity Mortgages in Windsor, Ontario, specializing in home and investment financing. From real estate investing to building a 20-employee brokerage, Scott shares mindset strategies for success. Passionate about overcoming fear and growth, he draws from personal experiences. Connect with Scott at lendcity.ca, call 519-960-0370, or listen for entrepreneurial insights.
Key Takeaways
- Embrace Risk: Treat business like real estate investing—learn from setbacks (e.g., bad tenants) as navigable "potholes"; familiarity reduces fear.
- Just Do It: Overcome initial hesitation by acting; like kids jumping into a pool, starting dispels anxiety—many guests echo this for success.
- Goal Setting: Write affirmatively (e.g., "I will succeed"), visualize as achieved; break big goals into small steps for ongoing motivation and accomplishment.
- Strengths Focus: Ask trusted contacts for strengths/weaknesses; prioritize excelling in strengths (95% effort) over fixing weaknesses (5%)—Scott discovered visionary connecting as his.
- Positive Mindset: Reframe negatives immediately; surround with positives (distance chronic negativity)—builds happiness and attracts success.
- Self-Improvement: Carve weekly time for books/courses/seminars despite busyness; Scott's recent read on structure led to hiring an operations manager.
- Delegate: Focus on vision/strengths; outsource weaknesses (e.g., operations) to work "on" the business—transformed LendCity from solo to 20 employees.
- 2025 Context: Amid AI/sustainability/e-commerce trends and easing inflation, resilient mindsets aid startups in tech/green sectors despite trade challenges.
Resources and Links
- LendCity Mortgages: https://lendcity.ca/ – Business financing and mortgage advice.
- Scott Dillingham Contact: Call 519-960-0370 – For entrepreneurship consultations.
- BDC 2025 Outlook: https://www.bdc.ca/en/articles-tools/blog/what-can-canadian-entrepreneurs-expect-for-2025 – Small business trends.
- Shopify Small Business Trends: https://www.shopify.com/blog/small-business-trends – 2025 insights on AI and e-commerce.
- CMHC Reports: https://www.cmhc-schl.gc.ca/ – Economic and housing data for startups.
Call to Action
If Scott Dillingham's mindset tips for starting a business in 2025's AI-driven economy inspire you amid job challenges, visit lendcity.ca or call 519-960-0370 for guidance. Share this episode with aspiring entrepreneurs—tag us on social media! What's your biggest fear to overcome? Leave a review on Apple Podcasts or Spotify to help others find 2025 trends, visualization strategies, or success mindset ideas. Tune in next week for more on growth and finance.
- (00:12) - Starting a Business Journey
- (09:13) - Overcoming Fear and Taking Action
- (09:23) - Seeking Feedback and Self-Discovery
- (13:23) - Focusing on Strengths vs. Weaknesses
- (17:11) - Cultivating a Positive Mindset
- (18:16) - Continuous Learning and Growth
Transcript
Introduction
Welcome to the Wisdom Lifestyle Money Show. I'm your host, Scott Dillingham. The show is designed to help Canadians invest better in Canada and the United States. We are the North America-based mortgage financing lender and provide education to both countries.
Discover how you can become a better investor and access the financing you need. Welcome back to today's show. I get asked all the time what it was like to start my own business, the troubles, tribulations, all the things, and how I made it successful.
So right now, obviously COVID's here. It's going to be here for some time, unfortunately. And there's lots of people that are losing their jobs. It could be from layoffs, downsizing, company closures, not wanting to follow vaccine mandates.
It could be any of these things. But the fact remains that there is a lot more job loss going on right now. Even when you consider Chrysler coming up, Chrysler is reducing some shifts at some of their plants. That will affect the local job market and all the off-spun companies that work with Chrysler.
The Core Idea
Job loss is a thing that's here right now, and we've got to get through it. So a lot of people are starting their new businesses and opening up their businesses, and they're asking me questions on how they can improve and make sure that it's successful. And they're asking me what I did. I think for me, what made it work for me at the very beginning was that I was used to taking on risk.
I would buy rental properties. I would renovate them.
I would rent them out. Sometimes I had bad tenants. I would get them out and put in new ones. And I just took every day and every risk, and I used it as a learning tool.
So I think that's the most important thing, is learn from the risk and grow and get past it. Because I was used to taking risks, starting a business to me, I did not feel any more risk or fear than buying a rental property.
Deep Dive
So for me, that was the same. But still, on my very first rental property, I did have a bit of fear about it. What if the tenants didn't pay, and I have to pay the mortgage? How am I going to do that?
And so there is that fear. But in my case, I was able to overcome it. So I would suggest to anybody out there that's wanting to start their business, is you just have to overcome your fear. Just like the Nike slogan, my podcast guests and radio show guests in the past have also said, just do it, right?
You just have to do it. And that step alone gets you past the fear. Once you do it, like, this is nothing.
This is fine. It's like my little kids, when they were scared to go swimming in the pool. Second, they jump in the pool.
Practical Steps
I love it. This is great.
So it's the same thing. Owning a business is the same thing, except a business does require a lot more of your time and continuous effort. And there's going to be roadblocks and things that come in your way. And you have to learn to get past them.
And I'll give you a perfect example. I think of business troubles, even life troubles, as a pothole. So when we drive our car over a pothole, it really sucks. Because it's loud, it's bumpy, it could cause damage to your car, and you have to pay for it.
But you can keep driving, potentially, right? Depending how big the hole is. Or you can learn and navigate a little bit better. And you can just drive around the pothole.
Key Takeaways
So then you're avoiding the problem or surpassing the problem in an instant, right? So it depends how you look at things. But we never just drive up to a pothole, have it hit our tire, say, oh, I'm done. And you walk away from your car and the pothole and just leave.
Nobody ever does that. But people do that with their businesses and with their dreams and their passions. Because every time in life, and I don't know why we do it as humans, even the thought has crossed my mind in the past too, and I have to keep reminding myself not to. But whenever we hit a roadblock in life, it could be that girl or boy you're trying to date.
It could be you want to start the business. It could be you want to ask your boss for a raise. It doesn't matter what it is. When we get scared and we let something stop us from moving forward, a lot of times we don't even attempt that thing again.
That fear holds us back and it stops us from doing what we wanted to do. So you really have to learn to never let fear consume you and take over your decisions. Because just like you wouldn't leave your car out the pothole because you hit a pothole, why would you just not ask for that raise? Why would you not start a business if that's what your dream and your goal is?
Resources
Again, it all ties back down to just do it, right? Now, again, there is risks involved.
There's fear involved. There's all these things. But once you do it just a little bit, you'll see that it's really not that scary. Now, another thing that's super important if you're going to get a raise, if you're going to meet that girl, if you're going to start your own business, whatever it is that you want in life, write it down and say, I will get my raise.
I will start my business and I will make it successful. But you have to write it down. There's something with writing it down. And everybody told me this and I never believed it.
I heard it at all these events I would go to for training, books I would read, and it always says, write it down. And my penmanship is terrible. Like it's worse than a doctor. A doctor looks like they have good writing compared to how I write.
Introduction
So I never like to write stuff down because it looks so terrible that even like a month or two later when I go to read it, I can't even read it. At the time it makes sense, but I just can't read it after. I was hesitant to write stuff down. But now whenever I have a goal or a target or there's something I want, I will write it down.
And that process of me writing it down, it visualizes and makes it appear real. And you got to think back. There's people that if you die in your dream, say you're dreaming, so you're falling asleep, you're falling out of the sky, let's say. We always wake up before we land.
But if you're falling out of the sky and you hit your whole body, your brain, everything thinks it's real and you can die if you actually die in your dream. So that's how real it is. So our body, our brains, everything think those visualizations are real. So you can use that to your advantage and visualize success and visualize your goals coming true.
And that will make them reality. And it sounds so crazy talking about it, but it is true. Anything that I've ever really wanted in life, that I actually wrote down what I wanted, sat down and visualized it. Like for me, for my visualization, I'll think about things when I'm on a run or sometimes I don't do it as much as I used to, but I would sit, I had this rocking chair, I'd throw on some headphones and I'd just listen to music and I would just imagine what I wanted from my life or what my life would look like.
The Core Idea
And I would sit there and think that it already had happened, right? Not like, how am I going to get this?
How's it going to happen? I just imagine it already happened. And then your body on autopilot will work to make that thing happen for you. Obviously within reason, you're not going to be able to flap your arms and fly.
It doesn't work like that. But you have to imagine real things that are within the physical keep of being, capabilities of a human being and just think about it and it will happen. And it sounds so strange and sometimes it can take a long time. For me, because I've done this and I always visualize things and write it down and whatever, it doesn't take me long to reach my goal, whatever it is.
But some goals can take five years, can take 10 years and you can't let that bother you. How you digest that, right? You have your big goal, your number one goal, but they actually say to keep going past whatever goal you set, keep going past that. Because if you set that one big goal and you hit it, then you feel that sense of accomplishment and then you no longer want to keep doing it because you already hit your goal.
Deep Dive
So you set the big goal that you want, but then you set crazier goals beyond that would it be even hard to fathom. But once you're at that super high level, those goals that might be unfathomable today, you will be able to reach in hits in time eventually. But the key is little steps at a time. Whatever your goal is, if you want to make 100,000 this year, don't say I want to make 100,000 in X amount of time.
And then if you don't hit it, get disappointed. The better thing to do so you have that sense of accomplishment is say, yes, I do want to make 100,000. I would like to make it in a year. However, I'm going to do it so I make 50 grand to start with.
And then once you hit that 50 grand, say, okay, now I'm going to go to 75 grand. And then from there, okay, now I'm at 100. So doing those smaller goals to get to your big goal will help create that sense of accomplishment for you. And it'll give you more energy to keep going and to keep driving.
That is the number one thing that I think a lot of businesses fail with is they set these huge goals and they get discouraged that they don't accomplish them in the time that they wanted to. So they give up. So it's better to extend that big goal a little bit. As humans, it's hard because we want it now.
Practical Steps
But if you can extend that goal a little bit and have smaller goals along the way, you'll hit them. Now, I got to take a quick pause, but when we come back, I'm going to continue about all the things that you need to do to be successful in life or with your business.
Welcome back. One of the things that I think is incredibly important to do is to reach out to people that know you and ask them, say, listen, I'm just doing this personal exercise and I would love it if you could tell me what you think my strengths are and what you think my weaknesses are.
Okay? And you want to find out what people think are your strengths. They might not be actually what you think they are. So it's a very eye-opening exercise because something that you think that you might be good at, someone else could see as your weakness and they could touch on what they think their strengths is.
And I've actually discovered from doing this that usually when someone else notices your strengths, they're probably more right on that than what you actually think of your own strengths because we have all these cognitive biases and different things and our thinking and things that we hear on the radio and whatever, it changes our perception of life and how we feel overall. But someone else will see you for who you are. Interview them, find out what your strengths are and get your weaknesses. Now, what you want to do with your weaknesses is you want to match that up with whatever your goal is.
Key Takeaways
Do you want that business? Do you want that Lamborghini? Whatever it is that you want and look at your weaknesses and say, all these weaknesses here, I'm not doing any of this to get my goal. Even if it's something that you could have improved on and made better, do not, and this is in my own opinion, okay, so everybody's different, but in my own opinion, do not focus on your weaknesses.
They're a weakness. Usually a weakness is something that you could be learned to overcome or it could be just something you just don't have that natural ability for. So to really excel, think of this, right? I'm six foot, I can run fast, but running fast is not one of my strengths.
It's, I wouldn't say it's a weakness, I'm in the middle and yes, I can train and yes, I can improve. Will I be the world's fastest runner?
I don't think so. But if I take my strengths, the things that other people see in me where I really excel and I just focus on that, that will get you to your goal so much better. So say, I'm trying to think of an example here, say, I'll actually give you one of mine. I didn't realize this in the past, but I'm a visionary and I'm really good at connecting things.
Resources
So doing this exercise, people brought that up to me and I didn't even know that about me. It just happened naturally and I didn't even think about it. But now that I know that being a visionary and I have these dreams and ideas and they always come to life for me and they can for you too. But knowing that is like one of my skills and specialties, I bring that forward to my business every day and it really helps propel us, I would say, above the competitors and it's amazing.
I started with just myself. Now we have 20 employees, right? And in the very beginning, the team was just hired to service my business and then I had a dream. I'm like, why would you do that?
Like, why don't you just build a whole team and everybody helps everybody? And so that's what it's transformed into. So when I first started Lent City, again, the goal was never to have 20 employees. I just wanted enough to handle my business.
But now it's so much bigger and better and it's all from visions and dreams and putting things together and meeting people and saying, oh, you'd be really good at this. You'd be really good over here and you just make it happen. Again, do not focus on growing your weaknesses.
Introduction
Yes, you can improve. Yes, you can make it better.
And you know what? Maybe you should. But in the tiniest bit, let's say out of 100 hours that you have, maybe do only five hours of improving your weaknesses. If you really want to improve them, if you really do suck at something and you want to get better, maybe give five hours out of 100 to improve that.
But the other 95, you should be focusing on your strengths and that's where you will excel. Another thing that I find people do still about mental, but people envision and think of themselves certain ways and they think, I, you know, I shouldn't be doing that. I shouldn't make that much money.
You know, why me? And that talk, even if you're not saying it out loud and it's just in your head, it will absolutely bring you down and it will become true because your brain and your body, whatever you put through your brain will become your reality. Think of the apple a day. If somebody is going to have a chocolate bar a day, what do you think they're going to look like in five years?
The Core Idea
Or what do you think someone that has an apple a day is going to look like, right? There's going to be a difference between the two and it's not something that happens overnight. So having a negative thought here, negative thought there, you don't think much about it. You're running on autopilot and you're whatever, it's just background noise.
But over time, builds up and will bring you down. So you do not want to have any negative thoughts. And it's hard at first, but once you start getting those negative thoughts, it could be about anything. Honestly, it could be your spouse, the way your kids act.
It could be anything. When you have those negative thoughts in your head, stop and change it. Change the thought and look for something good with your kids. Look for something good with your spouse, with your business, your job, your boss, like anything.
And you will naturally, it will actually make you happier because you're getting rid of the negative and putting in the positive. So you're going to become happier, but also you're creating a winning mindset for yourself. And that is going to create success in any area of your life that you want. So just starting a business doesn't mean you build a little stand and start selling lemonade at the corner and it's going to sell.
Deep Dive
There's so much more to the business. And I think most of it, at least on my end, was mindset. I was a real estate investor and I bought my building. So for me, whatever, that didn't mean anything when I bought, you know, the Lenz City building, that does not mean I have a business.
Then I started doing the mortgages out of it and just doing mortgages there. I still do not believe that's a business. The business, in my mind, encompasses your whole mindset and everything. If I had a mindset that I was a loser and that I was not successful and that people wouldn't come to me for mortgages and that I sucked, I would.
And I wouldn't do anything, right? But I don't have that mindset and it's also contagious, right? If you're always negative, you're going to attract negative people to you because everybody wants to be around people they're similar to. But if you're positive, you're going to attract a more positive crowd and then you're going to, you're going to see that there's people that are around you that are negative and you don't like it because it brings you down and you were there before but you don't want to be there anymore.
So you've got a almost hard knock life scenario but if someone around you is bringing you down, you need to spend less time with them because you need to be with the most positive in all aspects of your life. And the other thing too though is I wouldn't just fully discredit them and leave them. You have to look and say, are they negative because I'm so negative? If I was more positive, would they be positive?
Practical Steps
Because some people are leaders and some people are followers, right? So you don't want to just throw someone out of your life but you have to look at it and see where that negativity is coming from. But if it's, you know what, I'm getting negative because I can see you're being successful over here with all the things that you're doing in your life and that bothers me because I'm not so successful so I'm going to be negative towards everything you're doing, every idea, that person's got to go, right?
They're only going to damage you being around and subconsciously they're trying to damage you because they're not happy with where they are. So you really have to look at it. So don't just tell someone you're not going to be their friend and get rid of them or get a divorce or don't do that but you have to look at the scenario and really see where that negativity is coming from and if it's someone that is actually going to bring you down and there's nothing that could happen that you could help with to improve it, distance yourself from them because you want to be successful, we all want to be successful but life is busy and the last thing I would say too is participate in courses, do some online training, whatever it is that your skills are, master them.
So look at stuff to do that. We are all busy but if you don't create even a couple hours a week for self-improvement, whether it's working out, reading books, classes, seminars, whatever, you're not going to get to that next level and we are so busy but if you block, just block the time out, tell your whole life, I'm busy at this time, I'm doing this over here, it's hard to do it first but once you learn to carve out your time, you'll be able to have that time all the time to grow and develop and really be the person you want to be.
So make sure you carve that time out. Again, as always, I thank you for listening to the show. I hope this one helps you. I was really coming from the heart.
Key Takeaways
I have a lot of people that are asking me for help with growing their business and how to be successful in personal relationships in a life and I thought I needed to share what I know and what I do. If I could take a picture right now, you could see me.
I'm surrounded by books. I'm in my home office with all these books everywhere and I'm the person that I don't like reading. I actually hate reading but I do it because I know it helps me to grow and I'm getting another expert's perspective on things the last book I read just to share this before we cut out but the last book I read just showed me how structure is important in a business. I've been someone who's always like all over the place.
I'm wild. I'm here. I'm there and I'm getting stuff done but now I'm trying to write it back. We're going to be hiring an operations manager to take care of that but that was something that I learned from the book so if I can have my operations manager always hold the team accountable in the different departments that we run and make sure everything's going more smoothly it's going to be better for the customer better for myself and allows me to distance and then to focus more on my strengths instead of running the business I can work on the business.
That was the last book that I read when it taught me. So every little book will teach you something and take that and use it and grow and develop.
Resources
Thanks again for listening. I look forward to chatting with you next week. Thank you so much for tuning into the show today. If you found value please follow the show and rate it five stars.
It would mean the world to me. And lastly all the resources that we spoke about are at the bottom of the show notes. Looking forward to seeing you in the next episode.