These Siblings Feed Off Each Other's Input to Drive Their Entrepreneurial Success

A serial entrepreneur recalls her early collaborations with her brother and gives tips on how to encourage enterprise-building traits.

learn more about Kelsey Ramsden

By Kelsey Ramsden

Opinions expressed by Entrepreneur contributors are their own.

As I huddled over an empty deodorant stick, refilling it with soft butter in the kitchen of a condo during a family vacation on Turks and Caicos, I finally accepted that my family was not normal.

My dad had presented how difficult it was to butter corn on the cob and I took the lead in finding a solution along with two willing product engineers: my brother Trent and my eventual husband Andrew.

Thus we spent Christmas Eve in 2002 "inventing" the Amazing Butter Stick that would butter corn and toast without dirtying a knife. The days of slippery butter sliding off utensils would finally be over.

Alas, I was the only one who found the solution brilliant. The others considered it rather laughable.

Related: How I Raised a Family of Entrepreneurs

Fishing for a solution. Four years after the Amazing Butter Stick was invented and put to rest in one night, during another vacation, a fishing trip to Canada's Queen Charlotte Islands, my brother Trent hatched an idea for a more comfortable type of men's underwear.

Apparently Trent had found wearing a survival suit all day quite a hot ordeal. So after he brought up the issue at dinner, we returned to his room and he literally mapped out the new product on a napkin while I lobbed random questions trying to help flesh out the product.

That's how Trent Kitsch at age 26 really developed Saxx Underwear in 2006 with patented side panels. He founded a profitable company of the same name and later sold the business.

Related: 5 Ways to Teach Your Children to be Kidpreneurs (Infographic)

The early hurdles of entrepreneurship. My brother and I started creating products and services when we were very young. Probably our first revenue-generating business was when we barricaded our street with some leftover construction barricades that my dad kept in the back of his truck. We swept about 700 meters of the street to a pristine clean that one could eat off of and then set up a couple of chairs to be a barricade at the end.

When 5 p.m. rolled around, we charged every homeowner to cross through the barricade and drive onto their street. We knew they would pay us because we were kids. I was 7 and my brother was 4.

As kids, I was bossy and Trent worked for me. Now that we have grown older, the tables have turned and flip-flopped since we have each taken the lead with different ideas and businesses at various times. (We collaborate on Tallus Ridge Development, a company I founded. He now runs it; I sit on the board.)

Today we are both entrepreneur adults with houses and kids. We jokingly brainstorm about developing tranquilizers for babies (for when they just will not stop crying) and how to make the world's perfect pickle and what the best hotel chain experience would look like.

Related: Are Entrepreneurs Born or Made?

How entrepreneurs are buffed and made. The lion's share of a person's capacity for entrepreneurship results from "buffing." I use the word buff because it is such a slow process over time so that one hardly recognizes it's happening until at some point, the shine shows. It's also possible to notice if the buffing stops dead in its tracks (undoubtedly because of fear) or if the pattern becomes deliberate (from concerted thinking about starting a business).

People are often confused in thinking that entrepreneurs are born this way. But my brother and I grew were polished into being entrepreneurs, having been raised in just the right kind of environment. My parents (both entrepreneurs, by the way) had a great mix of street and book smarts and set high expectations and held us accountable while being our greatest cheerleaders and encouraging our sense of humor. We were taught to work as hard as we can, respect people and opportunities and never forget that at the end of the day all we have is our integrity -- and that rules are mostly just guides.

Here's how my family nurtured not one but two entrepreneurs. Perhaps some of our practices might resonate.

1. Looking for problems, seeing them as opportunities and talking to anyone who would share their ideas. People at the subway stop became fair game as was anyone sitting on an adjacent airplane seat.

Be open to people and opportunity. Geat ones turn up where least expected.

2. Allowing chaos in. We let stuff happen that would help us see problems close up

We never checked the car's tires before a cross-country road trip. So we would get three flats about 100 miles from civilization. That's how my brother and I came up with lots of marketabe solutions to problems. We tested and retested this sometime around 1986, 1991 and again in 1995.

Try to limit the amount of controls put into place. Some variations are needed in the system to allow for new discoveries.

3. Setting huge goals but planning fine details at the last minute. This allowed us great flexibility and to incorporate current knowledge of the market, data, client wants and needs right up until the product launch.

(Note: Christmas presents are best purchased the afternoon before Christmas Eve.)

Know the direction of a project, but too structured a plan will result in failure if there's no allowance for adjustments along the way and right up to the last moment.

4. Never considering anything normal or weird. We did not focus on the norm or what standard procedure was. Rules were there for interpretation, unless tweaking them meant jail time. We keep every solution open as an option.

For example my mother told Trent, 12, and me, 15, one morning, "I locked the keys in the house, darn it, and I have to get you two to school.

"Ugh, my AAA account ran out and to renew is going to be $150, plus we will be late. One of you kids take this field-hockey stick and break a bedroom window. It will cost less than $150 to repair. No one will break into the house way out here and we won't be late for school this way."

Try to not put everything into classifications or boxes. Remaining nimble of mind allows for innovative solutions to be possible and reasonable.

5. Asking why not and then after the answer comes, asking why again. Remember Chevy Chase in 1983's National Lampoon's Vacation? Don't go so far as to take the Griswold family's zany approach to life to ensure being buffed into an entrepreneurial readiness (though I incorporated a family business using the Griswold name.)

Asking why not first allows for getting right to the obstacles of an opportunity. Asking why after that then helps identify biases and assumptions. This is often where brilliant disruption occurs, resulting in marketable ideas.

Incorporating this kind of thinking or framing the world in these ways will be the right track to helping disprove that entrepreneurs are only born because they are, in fact, made.

Related: 10 Things Your Mother Taught You That Will Help Your Business Grow

Editor's Note: This piece has been updated with additional details about the author's parents and brother.

Kelsey Ramsden

CEO of Mind Cure Health

Kelsey is the President & CEO of life sciences company Mind Cure Health Inc., where she leads an innovative team providing psychedelic-assisted therapies. She has built multiple 8-figure businesses from the ground up and has twice been named Canada’s Top Female Entrepreneur

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