Carissa Reiniger is an entrepreneur on a mission to make small businesses more successful. When she was just 22 years old, after interviewing 365 small business owners in 365 days and hearing their financial struggles, she refused to believe that you have to choose passion over money, or money over passion. So, using her own small business, she set out to help her fellow business owners make smarter (more profitable) decisions and raise the profiles of these operations and the huge impact they have on the nation’s economy. Her advice to Young America? Think of a small business as a big opportunity.


Tell me a bit about your background.


I went to the University of Alberta where my original plan was a PhD and a career counseling juvenile delinquents. After about a month in school, I realized that there was no way I could be in University for nine years. So I worried less about grades and more about experience from that point on. I worked four full-time jobs, two volunteer gigs, all while taking five classes. When I graduated, I had a resume that made me look a lot older than I was, and I was trying to figure out what to do next.


Then I decided to go to the only big city in Canada where I didn’t know anyone. I moved to Toronto and worked in advertising for a year, and I started going to networking events. I started meeting a lot of small business owners — people who chose to pursue their passions, worked extremely hard, and were not making any money. I refused to believe that you had to give up passion for money or money for passion; you should be able to make money doing what you love. So, I quit my job in April of 2005 and decided to help small businesses make money doing what they loved. That was seven years ago, I started Silver Lining and here we are.


What was your first entrepreneurial experience? Lemonade stand or the Canadian equivalent?


I had a lot more leadership experiences than entrepreneurial experiences. I put a lot more of my time into charities. I don’t have the lemonade stand story, but I was always on student council, or the leader of the division or the club fair. Silver Lining was my first true business venture.


Tell me about Silver Lining. How did you come up with this business and the SLAP, its main product?


That first year in business I was 22, and I realized I had no idea what I was doing. I decided I’d interview one small business owner each day for a year. I talked to 365 small businesses in 365 days. I loved trying to figure out the patterns in small business growth and, more importantly, trying to understand why it was so hard to make a small business grow.


It didn’t resonate with me that 90 percent of people who started a small business couldn’t make it work. Through my conversations, it became clear that small businesses have two challenges that they are constantly struggling with — cash flow and capacity. They don’t have enough of either.


They always said if they had more time, they could make more money, and vice versa. This is what I call a “Cash Flow Capacity Catch 22.” Once I identified that this was the problem, my next question was trying to understand how they were trying to solve it. What I found then and continue to see now is that they typically do one of two things:


1) They hire a coach or consultant.
2) They hire junior level staff to work for cheap.


With the first option, they are getting strategy but not execution, and with the second option, they get the execution but not the strategy. And both require more time from the owner. So they end up spending more time and money and not getting what they need. Their attempted solution is perpetuating the problem.


So I asked, “How do we help small businesses make way better decisions about how they spend their time and money so that we can increase their success rate?” I created the SLAP™ (Silver Lining Action Plan), which is a business methodology that helps small businesses with revenues between 100K and 2M set and hit their financial goals and ultimately manage their time and money better. People have called the SLAP™ the Weight Watchers for small businesses.


What is it like to be a small business yourself, but in the business of counseling other business-owners like you?


Well, my learning curve has been phenomenally fast. Most small businesses spend all of their time thinking about how to be amazing at what they do and running their business is an afterthought. I have spent the last seven years thinking only about how to best grow a business. It gives me an advantage as a business owner. I learn a ton from our clients every day.


What is your favorite personal success story?


One of my favorite successes was on our five-year anniversary. The well-known statistic is that most businesses don’t make it to five years, and if you make it longer, you’ll probably make it long-term. So to celebrate that, we threw a birthday party on April 25, 2010. Everyone had to wear silver; it was a classy, simple cocktail party. Partners came, clients, old employees. It’s one of those things where you look around and can feel pride that this entire community of people stemmed from something that I created from scratch.


I remember very vividly sitting in the corner of the room and looking at all the people there and thinking about all these amazing people I had in my life.


I see that you’ve also helped start or invested in other small businesses through CR Inc. What is your criteria for deciding if a small business can make it – or not?


First, it is important to know that I think you can make money doing literally anything. Anything. So there is no business that simply cannot work.


That being said, my criteria is pretty straightforward. Is this company solving a real problem? Will having this company around truly make the world a better place? If I can say yes, then I look at the entrepreneur. Is this someone that I am willing to back? Would I want to go for dinner with this person? When things are amazing and when things are hard, do I want to go through that journey with this person? If I can answer yes, I get involved.


As you know, this week for Daily BR!NK, we’re focusing on the #FixYoungAmerica movement. What is your role with FYA, and what are your goals for this movement?


I wrote a chapter in the book they’re releasing and I’m a partner in GenY Capital Partners, which is a venture capital fund that came out of YEC. I want to help spread the message that getting involved in a small business is a viable career option for young people. It’s been true in the past that the more education you have, the better, and the more success and security you will have. But the world is changing, and big businesses are shrinking. The answer to that has been to promote fast growth entrepreneurship as a viable career option — but we are missing a huge part of the conversation.


To Fix Young America, we need to get this generation into small businesses.


I’m really intrigued by your extracurriculars, like volunteering in Africa. Tell me more.


I have 52 kids in Uganda that I help care for. I went down in October of 2006 and I gathered a group of friends and we went to Africa for 14 days and helped these kids. When it was time to leave, I found I couldn’t just say goodbye. So I made a 19-year commitment to help support these kids until the youngest one is out of post-secondary school (when they are 22). I go see the kids every year. We do different fundraising efforts, volunteer, we have a couple of staff on the ground who work with the kids, and our goal is to get them to be self-sufficient. They’re amazing, and I feel like they’re my kids.


What can Daily BR!NK readers do to contribute to your success and the success of #FYA?


For all the readers, I have two requests.


1) Support small businesses. Buy from them, thank them for how hard they work for the economy, support them.
2) Really think about this huge segment of the business sector. If you are looking for a job, don’t only look at corporations or tech start ups. Look at a small business. Small businesses need much better access to talent, and talented people can contribute in a significant way. Get to know small businesses. Take five small businesses out for a coffee and learn about what it takes for them to do what they do. I guarantee you will develop a deep sense of respect and appreciation for all of the small businesses out there.




Carissa is looking for:
small business support
Silver Lining Limited
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