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A Woman Entrepreneur’s Take On 25 Years in Business

June 1, 2021 marks 25 years in business for Tenato! I was just 26 when I got started, and I didn’t know much then, but I thought some of you out there might enjoy a highlight reel. You know, to give you the flavour of what it’s been like having a career as a woman entrepreneur, or mompreneur as many say, now having finally reached such an important milestone.

Before the Business

After graduating from University of Calgary in 1992 with my Bachelor of Commerce majored in marketing, I expected a glamorous marketing career awaited me. Instead, I ended up with a job in a small company, and a job description of “just do whatever it takes to bring work in the door!” While I thought creative marketing techniques would be my hallmark, I realized that success required something else: learning how to cold-call my rear-end off.  

At least one of my customers turned out to be super nice fella, whom I later married.  

But that job was not to last. As I got good at sales, the company couldn’t produce the jobs on time. Not to mention that the boss was always trying to corner me and convert me to his obscure religion – which preached females always yielding to male counterparts…shudder! 

I soon quit and went to work for a much larger company, figuring they wouldn’t have those same problems. It turned out they had a bigger problems.

A baby and a business

The big company was in political turmoil internally as its industry was transitioning to digital, and they laid me off when I was 6 ½ months pregnant. I felt something was askew, and I hired a lawyer. Though no wrongdoing was admitted, I got just enough settlement, after lawyer’s fees, to buy a laptop, and to last a few more months without working.

The nice fella I mentioned above (Gary) and I had just gotten married and moved, and I was staying home with the baby. I needed and wanted to do at least some work, but I could not bear to put my son in a full time day-care situation. Were there part-time marketing jobs? Flexible jobs? Work from home jobs? I remember a woman employer admitting to me in an interview, “I’d hire you right now, but if I gave you flexibility to work at home, I’d have to let everyone do that!” (That’s one thing I am so glad today’s pandemic has done for women!)

Hubby and I chatted; it seemed like there was no such thing as a good employer for me, so I thought “I know something about marketing, could I freelance?” Gary spurred me on. The idea was to get away with a few hours of babysitting here and there with a neighbour. Gary was working full-time elsewhere, but he offered to help me with doing the books, moral support, and anything else I needed.

The “START” gate

Facing my biggest fear (just plain “starting”) – I called the business “START Marketing” and decided I would focus on small businesses. Luckily my years of cold calling practice came in handy. I joined the Chamber of Commerce, scoured the papers for new business announcements, attended every networking function I could find, and called contacts from previous jobs. 

Slowly I rounded up a bunch of piecework…a brochure project here, an ad design there. I tried to give to advice here and there, but I often had the distinct feeling no one really respected my opinion. I was so young, and perhaps more a “pleasant distraction from work” than a serious consultant. Many called me their marketing “girl”, but it never sat well with me. I craved respect, and to be listened to.

The thing was, the project work I did, while appreciated, never really seemed to have a great impact in growing any of my clients’ businesses. Honestly, it was more like glorified administration.

A watershed moment

One day, a client with a print shop asked me to make him a brochure. I did just what he asked – writing and designing it with the information he provided, as I’d always done to that point.

When I delivered the design to him, he said, “Great, but who do you think we should send it to? And, do you think I put the right prices on here?” I realized, oh crap, I should have made him do it right the first time! I should have done research on the prices first, and decided the target market!   

Then he said, “Maybe you should help me do a marketing plan first! Get me a proposal for that!” and to me that was a double crap – I guess this means I am going to have to do formal proposals for all this kind of work!    

It really took me awhile to get my head around doing that. Because I didn’t want to have to do a proposal and not get paid for it. There was a time I even tried to charge for proposals, as they seemed like such as hassle.  

But on the upside, I was excited that I might be able to actually charge to do a marketing plan. Despite having learned how to do business plans and marketing plans in school, I never thought a business would pay to have one developed. After all, didn’t they just want the tangible things – like the ads and brochures? Happily, this was not the case. 

I was soon doing marketing plans, and full business plans for many small businesses. I raised my rates, and restructured my price model. I began selling clients what they needed, not what they asked for. I was finally learning to consult.

Baby #2 on the way

Five years in, I was expecting baby #2. What should I do? Wind the business down, or find a way to set it up to be less dependent on me? 

I decided to try the latter. I hired a full-time assistant and set up our first office within a business centre – one of those places with a shared receptionist and individual offices you can rent out. I rented her an office – and I worked at home.

My assistant, Angela, was a smart young marketing grad, who was a tremendous help. While she handled a lot of the project work, I worked right until the day before the birth of my daughter, and was back in meetings two days later! Luckily these weren’t full days, but it sure tested my strength.

Since I brought the baby along to many meetings, I made her business cards, which were a fun talking point. The clients who were comfortable with the mama/baby team stuck with us. Those who didn’t moved on. (Hence her title as “New Client Screening Agent”) We would roll into elevators and into big boardrooms. I would get the breastfeeding done right before the meeting started, and she would sleep right through.

I do distinctly remember the last day I took her to a meeting though. This was because instead of just sleeping through it, she was really active, and I had to stand for a 2 hour meeting, directing the discussion and bouncing her on my hip. I realized I couldn’t just keep bringing her, and still expect it to not affect my focus at the meetings. It was a sad moment in my working mom career. (Oddly, at the next meeting, without Lizzie, the clients were all asking “aww, where’s the baby?”).

I also remember a moment when I had temporarily loaned my pen to a client in a meeting, and then needed it back to jot something down, and I held up my hand to him and said, “Ta ta.” Whoops! Good thing he had a sense of humour.

And so the day-care (albeit part-time) days began….which was a lot of hustle in the morning and driving like a maniac to pick her up on time! How I never ended up in a twisted pile of metal on Deerfoot, I’ll never know.

Moves and more moves

The business centre we were in suddenly closed, and kept our damage deposit for no reason at all. In fact, they said they were bankrupt, but the company exists to this day – so someday I am sure the karma will come back to them.

I was too busy to fight over $700, and we moved to another office centre on 11 Avenue, which was a terrible parking-meter-parking-ticket zone.  With my hustling to/from meetings and daycare, I got about 5 tickets a month!  Not to mention that we got stuck with a receptionist there that had a penchant for being snooty to clients. 

After a year, my lovely assistant Angela ultimately decided to get married and move back to the east coast, and I was left wondering what to do and where to go. I literally scoured the city looking for a new office for my small one-person show while I sought out a new assistant. I found both, but the new assistant left after a very short time, and since we were ill-matched, I’d had my eye off the ball and was cash-strapped.

Gary got me a new Blackberry, which at first I was reluctant to adopt, but soon became completely hooked on. I considered it my new, more economical assistant, and found a contractor to help cover the phones part time too.

By that time we had moved to an industrial area (on Cleveland Cres SE), but when a larger tenant wanted more space we got the boot again.  

I remember wondering, “Doesn’t this city have a place for me? Why is it so hard to find affordable office space?” Until one late afternoon, I was looking on a warm day with the top down on my little convertible, looked up and saw a sign. The upper level of the Garry Theatre in Inglewood was for lease! What a chance. It was perfect. I grabbed it, and moved in there in 2005. 

Post assistant #2, could I have just gone back to working at home? Yes, but I noted the credibility factor with clients was so much improved with an office, I did not want to go backwards. Clients loved the new space, and it helped us transition into a stronger, more profitable rate-structure where I could get away from justifying hourly rates.

Stormy weather

In 2006, our family went through a kind of crisis, and my husband and I ended up adding a couple of new family members (one 8 year old, and one 13 year old) into our home. Helping these new additions to the family was very rewarding, but the situation drained my energy to the extent that I went about a year without gaining any new clients, and losing several, especially the ones I found more difficult to please. 

I learned that in the profession of marketing strategy/growth consulting, it is absolutely critical to show full energy and enthusiasm for someone’s business. And that year, I didn’t have it to give. Somehow, I hung on. I remember cutting various expenses, including my marketing expenses (since I was obviously so incapable of closing deals), which it pained me greatly to do, but I had just enough business to keep the doors open and to keep paying the rent. Fortunately, I never had to take money out of the family to float the business, it kept supporting itself and paying, me albeit at the bare minimum.

Behind the clouds, a next level

When the family situation resolved, I suddenly had a boost of energy. 

I took the chance to enroll for my MBA, because some of my clients had theirs, and I definitely felt my credentials should be at or above theirs (or why hire me as a marketing strategist?).   

Oh, how I wanted to go to a prestigious university like Queen’s or Harvard, but I still had kids at home, and I wanted to be able to get some real in-class time, so it was back to U of C for me. I got a partial scholarship and did respectably well on my GMAT, despite having no time to prepare for it. I decided I should be glad to get an MBA, and not get hung up on which school it was from. I was in, and I was going to get it done, while continuing to run my company.

(A few years later I took a Continuing Ed Leadership course at Harvard, and didn’t find the quality of instruction any better than U of C! While the students came from around the world, the instructor certainly wasn’t nearly as good as some I’d had at U of C.)

The MBA courses showed me just how far ahead my understanding of marketing strategy was after about 15 years of consulting, and also gave me some new ways of thinking. Mostly it boosted my confidence a lot.

Some of you may know that I am also performing musician, and around that time I had transitioned from being a side-player in other bands and to fronting my own four-piece band and doing a lot of shows as well. The day I defended my MBA thesis, I hustled down to the Stampede Grounds, and my band played for the U of C Stampede Alumni barbeque. Good for Gary – he learned how to do sound along the way and made all of this possible!

Recession and Transition 

Anyone will remember the bust of 2008, but it didn’t hit our business right away. 2009 seemed just fine, but by 2010 alarm bells were going off. I felt I could not blame the slump on just the recession.   

It had also been a time of major changes in the industry – social media and digital marketing were taking over like tidal waves. Companies were no longer searching for “marketing consultants” – I felt strongly that they were searching for “social media” or “internet marketing” experts instead. 

Although we offered these services, they weren’t in-house strengths. We (I) needed a change. Further, I was using a graphic designer who did not do web design, and separating these jobs was awkward. 

Then, an entrepreneurial young designer came along who could integrate all these services. We decided to help each other, and he taught me a lot about web marketing and SEO. We co-promoted each-others’ capabilities and found that this really helped both businesses. Things were looking up again.

Time for a re-brand

It was this young designer that told me our brand needed an overhaul. I remarked that all the incoming leads seemed really small, and he said, “it’s because your name is “Start” – it sounds like you do just small, start-ups.” 

What an eye opener this comment was! 

Although I’d always loved the ring of “START Marketing” I decided to take a page from my own strategy book, and find a new name. I scoured for ideas. I literally read and considered every word in the English dictionary. 

The word “tenacity” stood out to me. Playing around with it – I realized it sounded a lot like a musical term “tenuto” – a marking on a musical note that means “to give a note it’s full value, and make it brought out to be heard.” That was a lot of what I was trying to do for clients! 

Having been in business for about 15 years at that point, I also realized that our business was far more about “sticking with it” – i.e. tenacity, than just “starting” something. When I put the name “Tenato” on a list with several other possibilities – my daughter, then 11 years old, picked it out immediately. That was it! And we were the only company to be using it, so voila, we got a dot.com domain to go with it – what good fortune.

Rebranding fallout

The name change meant I had to invest in a new logo, website, and re-ranking the new website on Google. I worked hard to make the website more credible to attract more premium clients (I started with subtle black and white imagery and more formal-sounding language, as I was fresh out of writing an MBA thesis). 

The young designer who recommended the name change brilliantly created the logo and offered to help with the search optimization too. I was worried about the transition and our rankings, but he assured me there would be very little time for Google to transfer the rankings to the new site. Unfortunately, and for unknown reasons, this did not happen.

The rankings dropped to nowhere, and even the web traffic we did get generated no leads. It took several adjustments (the writing formalization had gone too far – so I dialed back to my more preferred, approachable brand style), and my writing a blog every single day for about 3 months. I also studied “SEO for Dummies” – making numerous tweaks – but I finally got there, and the business hung on.   

Did I mention that I also made quite a few cold calls, which I have never been above doing when needed, or when a special company catches my attention! Can’t take the salesperson out of this entrepreneur.

Turning a tight corner

When we rebranded to Tenato, we also decided to seek out key resources to build out the team and market as a group. 

I invited a few highly-experienced people to join me as “associates” – preferred contractors under Tenato’s banner as a team. These talents in research, creative, design, social media, web development, public relations and digital marketing gave me a deeper understanding of different facets of marketing and improved our services tremendously.

We now had a formidable team that helped us attract much stronger accounts than we ever had before. We were on the right path!

A key resource breakthrough

All of this momentum allowed me to hire another full-time resource – a talented graphic designer/illustrator who is still with us today: Samantha Boone, our art director. It took me a little while to get used to being someone’s full time boss again. Without Samantha, I would not have bothered getting a regular pro cleaning crew (did I mention the Garry Theatre is a dust-pit that I was struggling to clean myself? Poor Samantha had to raise the red flag!), employee benefits, and setting up proper employment procedures.

Having Samantha’s many capabilities in-house allowed us to revamp all our proposal formats, branded materials, and generate deliverables such as market research reports, branding guides, and design work that was best-in-class. 

All of this allowed us to win more work, and become more profitable. We were swinging for new heights and winning!

Hubby joins full-time

My husband Gary, while faithfully handling the company bookkeeping (not to mention being sound-man for my band) on the side of his full time career in software/aviation, finally had the opportunity to join Tenato full time in 2016 when the aviation company he worked for took a side turn. 

I was thrilled and nervous to bring him on board – as doing so would give us so much more freedom to set our own hours and take holidays; but it also was scary to wonder if the business could completely support the family.

The first couple of years were pretty stressful, as any husband/wife working duo will tell you. We had to learn not to talk about work 24/7. He has to get used to the uncertainty of cashflow. And he had the pressure of learning how he would contribute, essentially inventing his own role in the business. It also took a while to reconcile the wife vs. boss vs. partner dynamic!  As a result, he did a lot of his work at coffee shops instead of the office.

Fortunately, Gary and I have always had huge respect for each other, an iron-clad friendship and complementary strengths and weaknesses…we just needed time to find our stride. And after a year or so, we did.

New capacity

Gary, while not at all a sales or marketing personality, turned out to be a lynchpin in Tenato’s growth. He literally took every task that I was not good at off my plate – financial, operations, IT systems, HR, administration, and freed me up to do what I was good at. This doubled my capacity. 

He was also a huge comfort to have nearby; whenever I had issues of clients not paying us, or giving me a hard time, he was there to lend his presence and strength. I don’t know whether it was his strength, or his strengthening my confidence, but it made Tenato feel stronger all around. For example, he helped enforce my diligence in getting contracts signed and sticking to them, instead of doing too many verbal agreements and the not getting paid for them.

The business grew a lot – and as Gary systemized things, I realized the value he was creating might get us to a point where we could finally document a consistent process for building strategy, and train others to do my job (the other associates to this point all had different specialties, but none did what I did, i.e. the strategy development, so I was always directly handling all the account management too). Our kids were now also in their teens, and everything was just plain easier to manage.

Thinking bigger 

In 2018, I hired a protégé to train who was a skilled MBA herself – and the process of training her made me realize that I was well beyond making up processes from scratch for each client. I had a lot of systems – they were just in my head.

With great input and ideas from her, we were able to document and hone our unique methodology. Another one of our Associates, an expert in metrics and reporting, also helped us systemize a ground-breaking reporting methodology. These were major strides forward. 

While my protégé left to start her own entrepreneurial venture in early 2020 (just before the pandemic), she left us in a great position for the next phase of growth.

The pandemic

COVID-19 was a shock to us, just like every other person. Our main objective was to keep all our clients in business somehow, as well as ourselves. We cut our rates and boosted our service levels to help wherever we could. We took goods in kind, we extended longer payment terms, and I even performed music to help a couple clients with promotional events.   

It wasn’t a great year for cashflow, but we were proud all our clients survived 2020 and a few even grew remarkably! We also got involved heavily in planning community spirit-raising events, which helped us get our name out to the community and earned us some valuable online reviews.

New team members

The tough, pandemic-repressed economy brought opportunity too. While some businesses were ramping down, we were somehow ramping up.

Potential team members came knocking on our door, and the documentation and systems we’d been building were a huge selling point in winning these alliances. We were able to add three seasoned consultants to the team in early 2021, each with their own industry expertise, but all fully capable of being senior strategists, meaning I could train them to manage accounts.

What a difference it has made. As clients have gotten bigger, it has helped tremendously to have experienced strategists on the team- someone else to check the logic, and share the pressure of getting it right. They are also giving ground-breaking input into how to improve and expand Tenato’s services moving forward.


Was starting a business a good way for a mother like me to work, and keep my life in balance?

I absolutely think so. When the kids were young, I was able to swing babysitting and daycare on only a part-time basis. When they later were in school, I worked my schedule of meetings around their most important events. I got to sing in their schools, ferry them to their art and karate classes, and skip work on those perfect weather days and sneak off to the park.

This kind of flexibility also allowed me to work in my musical pursuits and complete an MBA.

Many of the clients and friends I have met have helped me in personal ways too: a PhD (Dr. Sisso El-Hamamsy) who helped my daughter with her math homework, a local celebrity (Theo Fleury) who coached a niece not to run away, a dietician (Andrea Holwegner) who helped me learn to feed my vegetarian son, and even the photographer client (Bob Hewitt) who shot all our family photos in the early years, including the one at the top of this blog! I marvel every night that I sleep on a luxury custom mattress from Sleep Boutique in the most beautiful bed from Signature Fine Furniture, with a glass of purified water beside me thanks to Instant Plumbing….and thinking how proud I have been to work with these great businesses! I could keep going on, but I feel I really owe so much in my life to knowing them, and to career that allowed me to choose to “help the good guys win” and make so many friends along the way. Plus, it has enriched my mind to learn about hundreds of different fields, and how they all contribute to our world.

In my view, self-employment is ideal for a woman who is not afraid of uncertainty, has a good dose of confidence, and who can roll with the punches. And, a truly supportive spouse is also a huge competitive advantage, as I’m sure I’ve explained.

Looking ahead

Will we continue to grow? You bet – we are always recruiting for those “just right” fits to our team. But if the pandemic taught us one thing, it has been to slow down a little too, and smell the roses. 

The kids are grown up and on their own now – one is a business owner, and the other is studying to be an engineer. That time went lightning fast, and I often miss it. But there will be another chapter ahead…hopefully with grandkids in it someday, and that will be pure joy too. 

This business has truly given me 25 wonderful years. Thank you to everyone who has been involved in Tenato’s, and hence my own, evolution. My career could not have been better any other way, and I am as energetic as ever about driving Tenato toward the years ahead.

If you’ve got a little anecdote or story about working with me or our team in the early years, we would love to hear it. Drop us a note – we’d love to hear from you.

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About the Author - Jacqueline Drew
Jacqueline M. Drew, BComm, MBA is founder and CEO of Tenato Strategy Inc., a marketing research and strategy firm with bases in Calgary, Vancouver and Toronto. With over 25 years' experience in all facets of marketing strategy, she is a business consultant, trainer and speaker who loves to use her superpowers "to help the good guys win."