Exclusive: Startup lessons from Canadian ‘unicorn’ founder and top executive Paul Teshima

How do you figure out the next right move in your startup journey? 

The kind that moves you from being heads down in building your product to ringing the opening bell at NASDAQ? For Paul Teshima, chief commercial officer at fintech company Wealthsimple, he encourages asking yourself:

“What experience is in front of you today that maybe won't be in five to 10 years?” Choose the one that's the most unique [...] I find that if you just do the same thing three times in a row, maybe you're really good at it, but maybe you don't get the breadth that could really make your life full.”

Teshima speaks from experience. The executive — listed as one of the best in Canada — went from growing a Canadian-born ‘unicorn’ acquired by Oracle to founding his own company used by the likes of Adobe and Shopify before landing at Wealthsimple.

While Teshima was in town, he sat with the Vancouver Tech Journal to share his story of pivots, adversity, and lessons learned, and how they all led to undertaking an opportunity to empower more Canadians with Wealthsimple.

Carving out his own path

Growing up, Teshima always wanted to be an architect. His father was a partner at Moriyama Teshima Architects, now a renowned firm with over 200 awards, including Canada’s highest architectural honour.

Teshima envisioned that he would one day take over his father’s role until he said something seemingly ‘strange’.

“He said, ‘Paul, the only way to really do well is to become a partner,’” Teshima recounted. “I said, ‘But you're a partner in your firm. Wouldn't that mean I'd have an opportunity?’ He just was quiet.”

It was then that Teshima decided to consider a different future. He always loved science and math, particularly using techniques to break down problems to understand how to solve them. This led him to study engineering physics at Queen’s University before pursuing a master’s in mechanical engineering at UBC.

“You don't have too many fields you can go into after engineering physics […] I wanted to broaden the opportunities I had coming out, and I thought mechanical engineering would be great.”

While Teshima was working on his master’s, he was already offered a position with the engineering company NORAM. It was a great opportunity, but Teshima turned it down. He received an unexpected phone call from his mom, who encouraged him to return to Toronto instead. Teshima was surprised as she had “never expressed her opinion like that” to him before.

“I think she thought that I was in engineering not because I necessarily loved it, but because I love solving problems,” explained Teshima. “So she was encouraging me to explore other opportunities before I kind of dive into one career,” adding that at the time, it “felt correct” and had he not listened, he might not have gotten to where he is today.

‘Falling into’ creating a to-be ‘unicorn’

Back in Toronto, Teshima ended up at Rogers as a manager, evaluating and implementing tech, products, and services.

While Teshima was “doing well,” he eventually left to become one of the founding members of Eloqua — one of the first marketing automation tools that modernized the marketing world. Teshima met the team from a previous consulting gig and took a chance on the startup as he was curious to “learn how to grow a business.”

Teshima played a pivotal role in leading Eloqua, overseeing the customer strategy and product. His contributions were instrumental in the startup's resilience, weathering two economic crises, raising around USD $35 million collectively, and eventually going public on the NASDAQ before it was acquired by Oracle for USD $957 million.

Eloqua’s success wasn’t the result of a “magic moment,” said Teshima: “It took us 13 years to build a public company that was at that unicorn level [...] If you really believe in something and you want to make an impact, stay focused on delivering against many things well.”

As with any business, Eloqua had its fair share of challenges. The company had to think and act quickly, especially in desperate times. 

Initially a chatbot for sales, Teshima and his team tried selling the product to everyone they could. They finally landed a deal at a ski resort that required a long trip to Mammoth Mountain. There, Teshima had to train the resort’s sales team on how Eloqua could be used to sell million-dollar homes to their clients.

“It was an absolute failure,” Teshima recalled. “We had tech issues [...] Online chat was not a tool salespeople used, and the clients on the website looking at homes did not want to engage in this way at all.”

The pivot that transformed Eloqua

Teshima felt Eloqua had reached its “lowest” point.

Then, one of the salespeople he was training shared a suggestion: “You know what I would like? If you could give me a list of every one of my clients who look at a floor plan, I would love to give them a call.”

Teshima was quick to call Eloqua’s engineering team. The technology was not only possible, but a prototype was ready to be demoed within 48 hours. It was a “huge hit” and marked the genesis of what’s standard in the B2B space today. Still, that didn’t mean things were smooth sailing from then on.

There were still some pretty “dire” moments, said Teshima. Building Eloqua at a time right when the dot-com bubble burst, there was no backing from VCs or government grants. Teshima and his team had to bootstrap to keep the lights on.

“I remember one time we were having trouble paying rent that if they were to shut us out of our office, we couldn't actually provide the service because the servers were there. In the Tenant Act in Ontario, they cannot lock you out if someone’s present in the office. So for five weeks, we tried sleeping in the office to make sure we could gather enough customers and payments to start paying rent again.”

Building Nudge.ai and letting it go

After Oracle acquired Eloqua, Teshima ventured out with co-founder, Steve Woods. Together, they raised CAD $2.8 million and launched Nudge.ai, a platform to help sales teams identify and build the right relationships to drive revenue.

Years before, Teshima and Woods came up with the idea when flying back home after closing a deal. It was a rare occurrence as Eloqua’s CEO had a rule where they couldn’t be on the same plane as it was “too valuable.”

“We were like, ‘What would you do next?’” shared Teshima. “We both said the same thing. Instead of working with marketing, we'd love to work with [sales teams]. We'd like to do something that's really product-forward in terms of how the product's built.”

According to Nudge, at the time, many organizations had sales “backwards.” They’d typically invest more in marketing collateral and sales training instead of building relationships early on and more often. There was also the habit of focusing on strong connections instead of weak ones, which research shows doesn’t expose you to as many different people and, in turn, bigger opportunities.

Over the next few years, Nudge would track over 40 million business relationships, acquire around 50,000 users with its free offering, and then provide pro and business levels. The product would garner highly positive reviews and be used by sales teams within companies like Adobe, Shopify, HP, and SAS.

Nudge would also raise around CAD $10 million collectively. But as the company looked for additional funding in its sixth year, Teshima and Woods made the difficult decision to cease operations. The reason was attributed to not discovering and pivoting toward a new use case until late and only recently starting to sell the product — leading to a challenging “next raise.” 

A few months later, Affinity, a San Francisco-based CRM startup, would acquire Nudge’s assets. Teshima and Woods believed it was “a good opportunity to let Nudge live on in a different business attacking a similar market.”

Biggest startup lessons learned

Looking back on his startup experiences, Teshima shared that one of the biggest lessons he learned was how to approach urgency.

“In the case of Eloqua, it was driven through being bootstrapped. We had no option, like sleeping in the office [...] In the case of Nudge, we took a little more time to get things right. So it was only towards the end that we really picked up the urgency [...] How do you maintain a level of urgency to try and add value to clients and grow your business?”

As for what’s been the most rewarding in building businesses, Teshima highlighted the journey rather than the destination.

“It's the whole process is where it's great. It's not just the company you build; it's the people you get to work with [and] the clients you get to service. So regardless of where the destination is, the learnings through [the journey] are priceless to me.”

For aspiring and existing startup founders, Teshima encourages being more open to asking for help and receiving support in different ways.

“We'd always just try and work harder to figure things out versus just asking for help. If I were to wind back, I would say ask for help more often from people from your network, your mentors. That can really fast track your growth.”

Teshima added: “If you get the right set of people surrounding you, whether it's through investments or a board of directors who really care about your business and understand what you're trying to do, it's incredibly valuable because it's very lonely as a CEO or co-founder to figure things out on your own.”

When it comes to balancing focus on your product and team, Teshima highlights the concept of servant leadership.

“Part of your job as a leader is to actually spend time with your team, not just manage them [...] A large portion of product today is obviously data-driven and quantitative, but ultimately in a new market, some of it gets down to whether a product manager has a sense of where do we need to go? What's the bet we need to make? That's not always going to be data-driven, but they have to feel supported to take that chance.”

“So it starts with that servant leadership concept to begin with so that your product leaders can actually feel they can go big and feel empowered to do that. They're going to make some mistakes, but that's okay.”

Joining and growing with Wealthsimple 

The year of Nudge’s acquisition would be the same as when Teshima moved forward with his next move: becoming Wealthsimple’s chief client experience officer to scale the client experience team, design programs to build client-advisor relationships, and improve the company’s quality and speed of response.

The serial entrepreneur always admired the company’s co-founder and CEO, Michael Katchen, leadership and values and previously thought, “If there's one person I'd love to work for coming off a CEO position, it would be Michael.”

Teshima admits that when Katchen first approached him, he wasn’t sure, given that he spent most of his life around B2B rather than financial services. He was quick to change his mind for many reasons, but especially because he “fell in love” with the mission of helping everyone achieve financial freedom, which to him was very “centring.”

“A little backstory for me: my parents were interned as part of the war, so they and their families lost all of their worth through that process. My parents taught me early on the value of saving and how to be focused on that and working really hard. I just thought it would be amazing to join a company where we could help a generation of people be better at that — that's what really drew me to the company.”

After three years with Wealthsimple, Teshima’s role transitioned to chief commercial officer as the company recognized the need to “pull forward.”

“In the client experience role, we were really focused on supporting our customers, helping them use our platform and providing financial literacy to them. What we realized is that there's a real opportunity to [...] help them with their overall picture.”

Teshima added: “Maybe they have an account with another financial institution, or maybe they're working with an advisor that doesn't pay them too much attention, but it's the advisor the family's used for many years. So this idea of [...] helping those people understand all of their choices and options and then adding value through that process became something that became more and more part of my role.”

Final reflections and takeaways for founders

Reflecting on his journey to date with Wealthsimple, Teshima highlights he recognized joining the company would be a ‘big opportunity’ but that it’s even more “mind-blowing” to him now, having talked to clients every week.

“Because they're using our product or they've started saving, they have a totally different outlook on their life,” Teshima explained. “They feel like they have more control, are not worried about certain aspects [and] can focus on other things. To me, a brand that gives that type of feeling to someone is unstoppable [...] There's so much room still to help more Canadians.”

What people may not realize about Wealthsimple beyond it being more than just a “robo-advisor” is that because it’s not a bank either, the company can move faster to respond to client needs.

“We're building a platform to manage all of your money, whether that's spending, saving, investing, or taxes. And not only that, we have people here to [support] you if you need a little extra help as well [...] We’re really trying to do something different than what's out there. Canadians don't need another bank — they need something better, and that's what we're trying to build for them.”

On the topic of innovation in Canada, Teshima shared some perspectives on the country catching up with others and some considerations for startup founders to keep in mind. 

“We're already starting to see this happen […] Canada has successful first-time entrepreneurs stay and become second-time entrepreneurs. It builds that layer of inherent knowledge in our ecosystem that helps the next generation of first-time entrepreneurs. I think it's just taken us a while to get those second and third waves in the ecosystem,” he said.

“I would say for me, the thing that I've learned and think is important to share is that a lot of the [success] stories you hear, and, hopefully, I haven't done this today, are kind of romanticized. These one magic moments. It's actually not that. It's a million small things that you just keep focusing on and doing every day [...] then slowly seeing an improvement over time.”

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