Everyone can be excellent for an hour…so only think and do things in 1 hour increments.

Yoli Chisholm is a pioneer in the Internet space first gaining online experience back in 1999 in Canada with start-up Chapters.ca that was the Canadian equivalent of Amazon.com. As a veteran of the offline retail world she brought her marketing and foot-traffic driving skills to Chapters online where she developed and grew one of the first Affiliate programs which grew to thousands of sites 9000+ driving traffic and revenue for the successful startup which got acquired by one of Canada’s retail success stories Indigo.ca She went on to work for Microsoft as part of the team that localized MSN in Canada. Yoli drove the launch of a number of channels including the MSN shopping portal, which was a key strategic partner for the biggest online retailers in Canada including eBay, Sears and Best Buy.

Wearing both the marketing and product management hats she drove the launch of the MSN Money, Games and Kidz channels. She ultimately ended up at the editorial and advertising helm of the #1 portal in Canada at the time responsible for the key network entry points homepage, Messenger, hotmail in both English and French. In this role she pioneered the development and implementation of the Customer Delivery Plan which was central to ensuring delivery of traffic to key channels and meeting advertising obligations for the historic Joint Venture between MSN and Bell Canadas Sympatico.ca Yoli was then tapped by start-up golden-child eBay to lead merchandising and activation at the height of the Internet boom. There, Yoli pioneered early customer segmentation analytics and solutions to optimize merchandising and behavioral targeting on the eBay platform to increase engagement, increase basket size and accelerate activation. eBay at the time was a young entrant to the Canadian market and quickly grew to be the biggest online shopping marketplace in the country.​ Always one with a passion for startups Yoli left eBay to join Points.com where they were building the wo rlds leading rewards management portal. There she is credited for redesigning and optimizing the redemption experience driving millions of loyalty point redemptions for key loyalty program partners like Starbucks, American Airlines and American Express. But her most significant impact was driving the acquisition and through-partner marketing strategy increasing sign-ups and conversions by 300%.

​ Also known for her passion for technology and a nose for the next big area of innovation Yoli spent some time marketing ringtones, mobile date chat services and dating websites for online dating pioneer Lavalife Inc. During this time Yoli managed relationships with the big telecommunications companies Verizon T-Mobile, Sprint, ATT and was one of the early advertisers on what were at the time up and coming Mobile Ad platforms like Admob, Millennial ​Media, Yahoo Mobile, and Google Mobile. She came full circle working once more with Microsoft at a start-up within the technology gia nt in the very challenging healthcare space. She and her team braved uncharted territory marketing Healthvault.com one of the early electronic medical record platforms along with a robust ecosystem of connected health apps and medical devices to consumers. In addition to driving the online marketing efforts Yoli wore the Product Management hat driving the teams that built the applications Healthvault Mobile and MSN’s My Health Info. Yoli then went to work in Microsoft’s US Central Marketing Organization where she currently steers US senior marketers to innovate in their digital marketing efforts across key business units Windows Azure, Office 365, Dynamics CRM, Windows 8 and more. In 2014 Yoli founded WELL Welearnlive.com where she is leading a team of 24 entrepreneurs as they develop 3 new businesses over the next 12 months (2015) in the Tech, Fashion and CPG space.

Where did the idea for The WELL Project come from?

There is this romantic notion that all “Brave and Bold” entrepreneurs must quit their jobs and along with their brave band of merry men hole up in a basement/garage or co-working space to build their startup. I actually think that for a certain segment being able to do that is a luxury and a privilege. There are people who have the desire and the skills to help build new businesses but don’t have the resources and support network. Along with that there is a segment of the population who simply cannot take the time or spend the money to go get an MBA. And lastly there is a segment of the population who don’t fit the profile of the typical personas who get accepted into most accelerators and incubator programs. The WELL project is modeled to meet the needs of all these underserved segments as a platform where people can learn about business as they build a business.

What does your typical day look like and how do you make it productive?

Essentially regardless of how my day goes it generally can be broken into these 4 buckets
30% thinking & Planning 30% writing & communication 30% executing & optimizing 10% Reading that ranges from intellectual to trash

How do you bring ideas to life?

The extroverted side of me loves to talk to others and bounce ideas off them. Sometimes I’ll drop a slice of an idea on someone I respect…gauge their reaction…then I’ll test it on the opposite spectrum like my kids or my friends who are not at all in the tech or business space and gauge their reaction… The introverted side of me will dig into research and almost lose myself in data and insights until a story starts to emerge…and in the end it is when there are trends in the data that intersect with my instincts or what I had organically felt was right about an idea that I will determine that it something I should work on.

What’s one trend that really excites you?

As a marketer what’s happening with data is almost like we are living CSI and potential customers are leaving their digital DNA all over the net and all over our assets and we get to connect all the dots and form a profile and a set of signals that tell us all kinds of goodness… the flip side of that is how do we use that data to create great experiences that deliver what the customer is looking for at the right time and do it so well that they become an advocate. I have always thought marketing is both an art and a science and have always enjoyed hanging out with the “Creatives” but now the cool kids are the data scientists and its exciting hanging out with them.

What is one habit of yours that makes you more productive as an entrepreneur?

I do not like to waste people’s time…whenever possible I think preparation is key. Be prepared and you will always be more productive.

What was the worst job you ever had and what did you learn from it?

Corn Detasseling. I was a teen in Canada and remarkably it paid about $18/hour which even by today’s standards is a great wage. Some people did one row and that was all she wrote for them and headed right back to the bus. I learned how to mentally entertain myself and think in shorter time blocks. That still serves me today. But boy did that job suck!

If you were to start again, what would you do differently?

Oh that’s easy….I would have paid attention in Computer class instead of dance class. I was a total nerd in the closet in high school. But with regards to entrepreneurship I wish I had understood then….that while talent and smarts can help you it is literally the “doing” that gets you further.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Everyone can be excellent for an hour…so only think and do things in 1 hour increments.

What is one strategy that has helped you grow your business? Please explain how.

When you are starting to build on an idea, be consistent, do something towards the business every week no matter how small it is….it’s like laying a brick wall even if all you manage to do each day is put one brick on the wall…by the end of the month the wall is higher than it was last month. It’s the same way in business – early adopters will stick with you if they see consistent progress. Those who have invested time and money into you stick with you if they see that gradual progress.

What is one failure you had as an entrepreneur, and how did you overcome it?

I have invested in businesses where I had no expertise and was reliant on others to make the business successful. I have found that when I focus on areas where I have some domain expertise and I can be the one accountable for success or failure I fare much better.

What is one business idea that you’re willing to give away to our readers?

I think individual paper mail is ridiculous the post office needs to be disrupted. Parallel to that I think banks should be reimagined to take over the % of mail that is relevant to finance and there should be a communication data type that is standard for bills, incoming checks, tax documents that is all managed through reimagined banks. Banks need to morph into entities that optimize people’s lives based on their incomes, skills, location and lifestage….Banks are the central hub that can see how people are living their lives…they can help people optimize their lives in more meaningful ways. Banks need to use their data to become life optimizers not the soul suckers they are today.

Tell us something about you that very few people know?

If I had to make a living another way I’d be a song writer.

What software and web services do you use? What do you love about them?

Legalzoom, Mailchimp, Google analytics, surveymonkey. Godaddy, wordpress, Office 365, 99designs, launchrock, Outbrain, moo.com, paypal, Windows Azure….and many others who all together help small businesses act like big businesses. They all have democratized business infrastructure and I adore them for it.

What is the one book that you recommend our community should read and why?

Winning the Story Wars by Jonah Sachs happens to be a book I am reading now….if you want to win in a competitive market, If you want to cut through the noise in a world where consumers and customers are inundated with messaging…the book has some thoughts on how you cut through.

What people have influenced your thinking and might be of interest to others?

SteveBlank.com, Garyvaynerchuk.com, sethgodin.com, timothyferris.com… I like common sense writing and insights that you don’t have to pay 50k a year in an MBA program to glean and put into practice. Grad Conn my mentor who I have worked with for many years has been a tremendous influence on me….he is hyper sensitive and adaptive to change and as a professional knows when to get on board what’s next and bring others along for the ride and yet he is an avid student of history – history of advertising, history of marketing, history in general…it’s a quirky combination that makes him an interesting person to work with and be around and in business it translates into recognizing the cues that the market is giving you that tell you how and when to optimize your organization.


WELL Project Website – www.welearnlive.com
Linkedin – http://www.linkedin.com/in/yolichisholm
personal Twitter – @yolichisholm
WELL Project – @welearnlive
Facebook – http://www.facebook.com/welearnlive
Youtube – http://www.youtube.com/welearnlive
Blog – http://www.welearnlive.com/category/blog/