Carissa Reiniger was 23 when she created Silver Lining Ltd., a company dedicated to helping small-business owners make more money doing what they love. From 2006 to 2010 Silver Lining Ltd was a consulting business, taking small business owners through the SLAP (Silver Lining Action Plan) methodology by having trained individuals go into the business and execute a SLAP on the small business owners behalf. In 2010 she began the process of evolving the business model from a services/consulting company to a software company. The company is now, primarily, a software company; but clients do have the option to enlist a coach or SLAP expert to come in and assist with execution for an additional fee. She is the author of several books, including “Inspiring Entrepreneurs: How to Build Your Business to Its First Million” (Silver Lining Ltd, 2008). Her latest, “Thank You Small Business” (Silver Lining Ltd., 2013), which has become the base for a movement to increase awareness and appreciation of the importance of small businesses.


Many people dream of creating global corporations, but you have dreamed smaller. Why were you dedicated so early to small businesses?

I come from a large family of very down to earth people who never had a lot of money. I was home schooled until grade 10 because I had a lot of anxiety issues. I tried to go to kindergarten but that was not a good experience for me. I was told I was dyslexic because I had a lot of trouble reading. I made letters backward and just didn’t pick up a lot of the things you’re supposed to pick up in kindergarten. I had a great deal of social anxiety.

I finally went to school in 10th grade, which was my own effort to confront my anxieties. I didn’t know a lot of people in my school, of course, so I ran for student council the second week of 10th grade. I was on a mission to meet people. I won the election and underwent a very rapid transformation into one of the most popular girls in school. I was dating the most popular boy; I was attending pep rallies; all of that.

That was a bold move for someone as uncertain as you were, wasn’t it?

It truly was. A lot of people who know of my early childhood think that it sounds very sad, and in some ways it was. I never had a sleepover with friends; I never went to camp or did a lot of things other kids did. I was sick all the time from anxiety.

So I wouldn’t say I had a typical childhood by any means, but I did have the privilege of learning at a young age that you can spend all your time worrying and wondering “What if?” or you can just go do it. And if you do that, chances are very good that you’ll go farther than you thought. And that lesson has been with me the rest of my life.

I’ve won big and I’ve lost big, but I go for it.  I don’t think I would have the gusto for that if I hadn’t learned that lesson early on in my life.

And what brought you to your interest in entrepreneurship and small business?

I received my B.A. in developmental psychology from University of Alberta. I had initially planned to get a Ph.D. in counseling but I realized that would take nine years of school and I just was not that much of an academic. I was too eager to get out on my own.

While working on my, B.A., I started working a lot. I worked three or four jobs during my last years at the university in addition to my course work. When I graduated I decided to move to Toronto, although I didn’t know anyone there.

Why Toronto?

I wanted to go somewhere where I didn’t know people. It was something I wanted to know about myself: whether I could do everything I wanted to do somewhere where no one knew me.

Right away, I got a job at global ad agency in business development. It was a pretty big job for someone my age and I realized that I was interested in business development and growing a business. I just liked the basic challenge of figuring out how to make a company make more money. I loved it but not the ad agency. With my degree I had wanted to do something in life that helped other people and advertising just seemed a shallow career to me.

I went to a lot of networking events so that I could meet people and I kept encountering small-business owners who were very passionate about what they did. They worked so hard that it was inspiring. Most of them were struggling with how to build their businesses.

So I knew people who made money but didn’t love what they did and people who were passionate about what they did but couldn’t make money. I believed it should be possible to be both passionate and successful. I quit my job at the ad agency. I was 22.

I started Silver Linings to help people make money doing what’s important to them. That was the simple mission I had. But I had no idea what that meant.

How did you get the business open? Did you borrow money?

No, I didn’t raise any outside capital. I just went for it. My first clients were my high school teacher’s husband, my university boyfriend’s uncle and one of my childhood babysitters. I realized quickly that it doesn’t matter what you know but who you know. There were so many people who were willing to believe in me and give me a shot because they knew me from other places. I realized the value of relationships.

Were you a success from the start?

Well, I was good at sales. We hit a million dollars in revenues our first year in business. We didn’t have a growth challenge like a lot of small businesses. We had an operations challenge because I didn’t know how to manage it. Our problem early on was cash flow rather than sales. And that’s dangerous. We were always kind of catching up to our sales, which is not ideal.

So you looked more successful than you were really were?

Oh absolutely. We’d grown really fast. I was winning awards and getting press coverage. I was this 23-year-old CEO who was working with all these well-known companies. It sounded so good but in the background I was worrying about how we’d cover our $80,000 payroll the next day because we only had $10,000 in the bank. I was so young; I didn’t know how to handle it. I didn’t know to ask for help because I thought that was embarrassing. It was a really interesting couple of years.

Was there no small-business counselor you felt you could go to or a mentor?

One of the ironies in all of this was that I felt pressure to know what to do. If I was going to be this business expert, I should know what to do. I felt asking someone else would discredit the work I was doing. My opinion on that now has changed so significantly and I have three tremendous mentors and business advisors who help my life in a lot of ways.

But I made a mistake: I didn’t know what to do but I just kept fighting to figure it out instead of getting help.

Do you find that’s the case with many of the small businesses you work with?

Yes, but it’s complex. My heart goes out to them. As a business owner you have a need to come to the world confident, clear, organized and ready to do business. There’s an element of posturing in that that I think is OK and maybe even required to get a business off the ground.

But if you fall into the trap of thinking you have to know everything, you won’t succeed because none of us can do that. One of the small-business issues is that you’ve got one human being trying to fill every executive-level position and that can’t be done.

There’s no way a founder should know how to do all the things that are required with a small business. What I tell our clients is to develop a small circle of people who you tell everything to. You don’t have to tell everything to everything. In fact you shouldn’t.

You should have a handful of people—no more than five, probably no less than two—to whom you can tell your best news and your worst news. I remember that when we hit $1 million that first year I couldn’t tell anyone because I was afraid of what people would think. But you need people with whom you can celebrate your achievements.

Was there a point where the news was so bad you thought you’d fail or you were tempted to give up?

Yes and no. I was advised a couple of times to give up. But in my mind that wasn’t an option. I was clear and determined that this was going to work some way, somehow. I have this motto: “How not if.” If I make a commitment to something then my thinking about it becomes “How not if.” Not “if it’s going to work” but “how it’s going to work.

We’ve changed our business model—and pretty significantly—more than once. We’ve moved between cities. Our journey has not been smooth. We’ve made mistakes. But I think we’re still here because of “How not if.” Every time we’ve encountered a problem, my approach has been “How can we make this better?” or “How can we solve this?”

It’s still true. One of the things I’ve been thinking about is that I don’t think I want to work with the company much longer. I’ve been doing it for eight and a half years and I think a founder’s job is done at some point. I think we’re almost there. But I’m also very clear that Silver Lings has a lovely life ahead of it. So, “How not if.” How do we tackle this next version?

Do you tell small-business owners to not give up too easily?

Yes. I believe what separates people whose businesses work and those who don’t is how tough they are, not how smart they are. I’d like to believe I’ve gotten smarter over the last eight years, but I wouldn’t be here if I only had all the information I’ve gathered.

I say that the two most important requirements for small businesses are passion and perseverance. And I don’t think you can drum up the perseverance you need if you don’t really love what you’re doing.

I keep going back to my belief that you can make money doing what you love. And I think I have influenced the success of many small businesses I’ve worked with. I want owners to know they can get through whatever difficulties they face. Whenever I refocus on why I started Silver Linings and why I care as much as I do and feel that it’s important, that energy comes back to me.

A lot of people start a business because they think it’s a good opportunity or that it will make quick money but not because of a passion. In those circumstances I do worry for them because I’m not sure they’ll be able to muster the strength needed.

Passion and perseverance are great but capital helps, too. Is it true that for many women raising capital is an especially difficult challenge?

It is. There are a lot of studies showing women aren’t able to raise capital as easily as men can. I didn’t raise capital. I used a couple of thousand dollars I had in the bank. By the end of three years we were $400,000 in debt and $300,000 of that was because we wrote off a lot of invoices from customers who couldn’t pay us.

For the size of our company, $100,000 was a reasonable debt load; $400,000 was not. But it was our reality. We spent the next three or four years paying that off. And then we did a dramatic shift in our business model a couple of years ago where we decided to build software. We budgeted it to cost $1.2 million dollars but it took close to a year to complete and it cost closer to $2 million. A year ago I had to raise about $500,000 in bridge financing and that was the first time we had to raise capital.

I look back on our journey first as a self-funded business, then having debt, then making a profit and then investing in a significant software project and I feel a bit like I’ve done it all. For a long time I had a great sense of pride about owning 100% of my company and about having built it myself.

What I see now is that there is a choice that everyone—myself included—has to make. And I haven’t faced the choice yet. But the choice is, do you want to build a business a little more slowly but funded internally? Or are you trying to build something aggressively and exit it? The level you’re trying to achieve requires equal parts time and money.

It’s a 100% possible to grow a business without raising capital. I’d say 99% of our clients never raise capital. I won’t say that’s easy, but it’s doable. I ran my business for many years like a small business but I thought about our vision and impact like a fast-growing scalable startup tech business. Those were not in alignment. What happened was that I couldn’t keep up with our growth because I hadn’t funded the level of growth that I wanted.

And so now I’m facing that choice with our next step. Do I go raise a lot of money and move the company quickly in the next direction? You have to know what you want from your business and be realistic about what kind of funding is required for the growth you want. Growth does cost money. The more growth you want, the more is required.

Is that next step for you the Thank You Small Business initiative you’ve begun?

One of the things I’ve seen in the last eight-and-a-half years is that being a small-business owner can be a thankless job. You have your family who would like to have more security, you have staff who want more security, too, and it can be lonely for the owners. They feel others don’t get what they’re going through.

I was writing my book, “Thank You Small Business,” and I realized that if you look at both developed and developing countries, small businesses are really driving the economies. Tech startups are creating false economies, if you will, because there’s money circulating through them but there’s not a lot of economic impact. Small businesses are the true lynchpins of economies. I was writing my book to tell that story and how we can support small businesses and help them grow.

The more I thought about it the more passionate I got about the idea that small businesses need a body of people who are their cheerleaders, who understand what they are going through and who are trying to meet their needs and give them the support they may not be getting from others.

The Thank You Small Business movement was born in January 2013. We call it a not-for-profit movement. It’s a company but all the money we raise is put back into the effort. We collect dollars from corporations, companies or anyone who wants to help and then we use that money to help support small businesses.

For example, we mailed 25,000 hand-written thank-you cards to small businesses. Inside there was information on our resource center like a webinar series on what owners need to grow. There’s a checklist that I wrote that lets owners assess their readiness for growth. When they get their score, there’s what we call a cheat sheet that gives them a ton of templates and resources and ideas for software they can use. Anything they can use and do to increase their score.

Shortly we’ll announce our plans for Phase 3 of Thank You Small Business, which will run from February 2014 to February 2015. We’re on a mission to create a movement that’s all about this “thank you economy” where all of us are doing our best to support each other.

We say, “At the very most, you can buy from a small business. At the very least you can say thank you.” We want business owners to feel a sense of pride in what they do because it’s so important. The rest of us can develop a deeper respect for what they do and how they work to build our economy.

Between this and Silver Linings, do you feel you’ve met your goal of making a difference in the world?

I don’t think I’ll ever feel like I’ve completely met my goal. I think I will always have deep desire to make a difference, whether it is just with the one person in front of me or on a global scale. I think Silver Linings does make a difference and that there’s much greatness ahead for both it and the Thank You Small Business movement. There’s more for me to do in life. I don’t think I’ll ever be done.

Is it true that one of your life goals is the fly a plane around the globe?

It is a goal. I only have 10 hours piloting in the air so I have a big chunk to do. Originally I wanted to fly around the world in 30 days beginning on my 30th birthday last year. The reality was that I had to raise capital for our software project and it was time to stay with that. My adjusted goal is to do it for my 40th birthday. It’s definitely on my agenda.

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