Jay Myer's Path to Bold Commerce's 1,000 True Fans

Bold Commerce's Journey From Idea to Scale

It was the height of the dot-com bubble. 


While Amazon exclusively sold books, music, and videos, eBay was the dominant retail marketplace.


To a savvy entrepreneur like Jason “Jay” Myers, this was his first golden moment.


Over 20 years later, Myers and his co-founders Stefan Maynard, Eric Boisjoli, and Yvan Boisjoli now run Bold Commerce. Bold Commerce has 20+ apps which help e-commerce entrepreneurs make more money online.


Today the Bold Commerce team serves over 100,000 entrepreneurs with their apps. But their business wasn’t always this big. Myers shares his growth ramp to get their first 1,000 true fans.

The Inspirational Idea for Bold Commerce

In 1998, Myers’s dad ran Heartland Archery in Winnipeg. It was a modest shop. Myers saw the opportunity to bring their business online. With his dad’s help, Myers brought their retail store to eBay.


Leveraging the eBay marketplace, Myers was able to quickly grow their online store. But as any successful 3rd-party seller will tell you, renting customers at a premium was a major frustration.


On top of eBay’s high fees, Myers realized he wasn’t building a brand. It’s not uncommon for people to shop for the lowest possible price. And loyal customers were few and far between. Myers had enough.


So in 2005, Jay started an e-commerce store.


While he saw some success, his profit margin was slim. 5 years later, he closed up shop and became an SEO specialist. But as most entrepreneurs will tell you, once you’ve got the bug, it’s hard to shake the euphoric highs and lows as a founder.


A month later, Myers launched a second online store, this time on Shopify. 


Soon after opening his doors, Myers got an email that his email marketing tool had a Shopify app. It was a smart move for Shopify. By creating a valuable core product with an API, entrepreneurs could solve problems and make money by helping Shopify customers. A win-win for everyone.


Curiosity got the better of Myers.


“Seeing the app store, I had a list of ideas to scratch my own itch.”


Without a background in app development, Myers couldn’t find a way to solve it himself. But he did not allow any obstacle to get in his way.


“I talked to a few agencies to build the tool for me, but it didn’t go anywhere. A month later, I told my friend Stefan about my idea.”


A few drinks at the pub and several hours later, they came up with a list of apps they wanted to build.


“[Stefan] knew of a couple brothers he wanted to bring onto the team. All we wanted to do was see if we can make some beer money doing this.”

The First Bold App

If you want a successful business, start by helping others get what they want. In turn, you will get everything you want.


“At the time, all other apps were back-end integration tools. They would connect your store to USPS, MailChimp, and other tools used in the business. Unlike the other apps, we came at the problem as a store owner.”


Like many co-founders, they began by scratching their own itch.


“I knew the Best Buy’s of the [retail] world live-and-die by upsells. So the first app we built was Product Upsell (now Bold Upsell).”


By solving his own problem, Myers was able to reduce his time on research.


“Living as a merchant for 12 years, I knew the pain points and what I could and couldn’t do. If you’re going into a space you don’t know, a ton of research is important. Is there a need? What’s the competitive landscape like? What’s the customer’s willingness to pay?


I was a merchant, so I knew this app would be valuable.”

An (Un)Scientific Method to Pricing Bold Upsell

It’s common for price to be an afterthought for early-stage entrepreneurs.


To be fair, most entrepreneurs do not know how to create a pricing strategy. And pricing services often cost thousands of dollars.


“We started by looking at other apps, what people were paying, where we fit in, and said let’s charge ‘this.’” 


“This” price-point was $10/month. As Bold Commerce developed more apps, they moved from cost-based pricing to value-based pricing.


“[An app] could cost you $1,000, but that doesn't mean anyone will pay a penny for it. Or it cost $500 and you are able to charge $1,000. Understanding the value you create shapes the price you can charge.


“If someone knows your tool made them $700 last month and they paid $19, then they’ll keep it. People need to know the value of what you’re doing.


“Everyone buys because it brings them value. A shirt may cost $5 or it may cost $100. It may cost the same to make it. But if the $100 shirt increases your social status and makes you feel better than the $5 Walmart shirt, that's perceived value, and it's still value.”


Editor’s Note #1: I don’t have an editor.
Editor’s Note #2: I agree with Myers. The best way to charge more and keep customers is to prove your value. But as smart entrepreneurs know, value-based pricing doesn’t determine your price-point. 


During customer validation interviews, you can find out a customer’s willingness to pay with a price sensitivity analysis. Once you have your price range, you can map your pricing strategy. If you are launching your first product, you should price it for market penetration.


Pricing your product is one thing. Shipping your product and getting customers to pay for it is another beast altogether.

Launching Bold Commerce

Success isn’t without its setbacks.


Myers and his team published their first app and uploaded it to Shopify. Within 24 hours, they got their first customer and their first negative review.


It turned out they forgot to upload one of the app’s instruction pages. This left the merchant with no clue how to use the app. This was a lesson that made a major impact on Myers.


Here’s what Myers learned in hindsight: 


“When you release a product, you need to get feedback from early users, talk to them, phone them, and watch them use the app. Then make adjustments, test results, and decide if this is worth continuing.


“Look at killedbygoogle.com. It lists every product killed by Google. Even the smartest people in the world don’t know perfectly what people need. You always need to iterate and assess your product.”


Myers admits they were lucky. Bold Upsell was a hit from the beginning.


“I feel we had product-market fit the moment we launched Bold Upsell. People were using it, loving it, and giving a ton of positive reviews. We couldn’t keep up with all the requests, in a good way.”


That doesn’t mean they could sit on their past success. Talking to customers was key to improving their product.


“With Shopify, when someone installs the app, we got their personal information. We then emailed everyone who installed our app to get feedback from them.”


But not every product they’ve launched was a success.


“Sometimes we had to scrap large portions of a product and keep one feature. Everything else confused customers. When we didn’t have product-market fit, we wanted to see where it created value. Then we doubled down on that functionality.”


How do you know what features your customers are using? You track it with analytics.


“We use surveys, Hotjar for heat maps and video recordings, had live calls with merchants to see how the use our app. We also use analytics tools to see what customers click what and database queries to see what functions people use. Our analytics tool stack includes Google Analytics, Google Tag Manager, Mixpanel, and Google Optimize.”

Growing Bold Commerce by Doing Things that Don’t Scale

One of the biggest failure points is trying to scale your startup too soon. This is especially true when getting customers early on.


“Shopify used to showcase the 40-50 new stores that launched that week. People would post their store on forums. We personally reached out to owners on Twitter and got some positive traction.”


This opportunity is no longer available. But Myers suggests using BuiltWith to find businesses that use relevant tools.


Editor’s Note #3: You can also use NerdyData to find relevant customers for interviews.


Once you’ve validated your business, getting new customers is a matter of showing up where your customers are. This can be done by mapping the customer journey.


“Where do people go before they buy a GPS for a boat? Maybe they start by watching Youtube videos. Then they do an organic search to compare products and buy a GPS.”


Editor’s Note #4: Content comparison pages are an excellent opportunity to test SEO and PPC. In my teardown of Bold Commerce, I estimate they are leaving $332,280/year by failing to do this for one of their products. I wrote about how to do comparison pages in “Comparative Advertising and Content Marketing: Applying The Art of War to Content Marketing.”


“For us, e-commerce store owners are only in a few places. They are in Facebook groups, conferences, on forums, and e-commerce platforms. Then we make sure we’re there.”


After launching on Shopify, pitching on Twitter, and a little PPC, Bold Commerce started to get 30 to 60 customers a month. At $10/month, Myers and his team could see the light at the end of the 9-to-5 tunnel.

Quitting the 9-to-5 Jobs for Bold Commerce

Life as an entrepreneur is easier when you don’t have a family. But quitting a stable job isn’t as simple. Especially without investor funding.


“We all had families. My wife was 5-months pregnant, and another co-founder just had a kid, another already had 3 kids. We all had mortgages and bills to pay.


“Our wives made a deal with us: once we could pay ourselves what we earned, we could do this full-time.” 


Not everyone burns the boats before becoming an entrepreneur. 


Riffing off of Reid Hoffman, Myers says, “You don’t have to jump off the edge and build a parachute on the way down. If you fail, that’s everything.”


By keeping their full-time jobs, the Bold Commerce co-founders removed a lot of risk. But that may mean you need to burn the midnight candle before you make it.


“We worked from 5pm-3am, used lunch hours, and doing this as a side hustle to de-risk it. There’ no need to quit your job.”


Eric Boisjoli was the first co-founder to quit his job. With a new child, Boisjoli was often working until 3 AM to ship the product on time. But in October 2012, he made Bold Commerce his full-time focus. A month later, Maynard made the jump full-time. Yvan Boisjoli joined the team two months later on January 2013. Myers was last to make the switch in March 2013.

The Role of Investors for Bold Commerce

There are two common philosophies about investor money.


The first viewpoint is investor money will allow you to go full-time from the beginning. This is what angel investors and seed funds are for.


The second viewpoint is investor money allows you to add more fuel to the fire. Bold Commerce took this approach when they took investor funds in November 2018.


“Up until November, it was all bootstrapped. There were tax credits and a few grants we could leverage in Canada, but the investor community wasn't as strong.


“If we were building software like Facebook, that’s a different story. The very first user doesn’t get much value at all (with its network effect). So Facebook needed a lot of users before an advertiser was willing to give them any money. But our first user was getting value day one.


“We’ve been fortunate to have an amazing board. Our investors have the foresight and clarity to create a roadmap, forecasts, and goals to help us know where we want to go. 


“When you’re in the forest, every squirrel looks like an opportunity. But when you step back as an investor does, they see the company as a whole and where you should go.”

Myers’s Advice to Early-Stage Entrepreneurs Getting Their First 1,000 Customers

Entrepreneurs often lack focus. Especially in the early stages of their business. 


People think focus means saying yes to everything you should focus on. That’s a quick recipe for disaster. Instead you need to say no to 100 ideas to say yes to the vital few.


“Focus first on getting your first 10 customers. Then 100. Then 1000. It’s not the same strategy for each stage of growth.


“Think of Airbnb. [In the early days], the co-founders flew to a new house and took the pictures so the rental would look good. They could do that for the first 100 or so. Don’t worry if something isn’t scalable. You need to do this to get a ton of feedback.


“Your first 1,000 customers are your best researchers. Listen to every single one. Stay close to them, learn from them, and be flexible.


“It’s okay if the first product fails at first. Facebook was a social network for schools. Google has expanded from search. There were 17 things we started before Bold. 


“Scaling is an important part of the process. But those first 1000 customers are critical to your research and the trajectory of your startup. Going one degree off-course in the beginning makes a huge difference down the road.


“9-out-of-10-times the product you first launch won't be the same as the product you scale. Start off by doing things that don’t scale first.”

Special thank you to Bill Widmer for making this interview possible. For more interviews like this, check out the series 1,000 True Fans.

Jason Quey

I am the CEO and Founder of Growth Ramp. I enjoy helping high-growth startups on their journey from idea to scale.

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