The founders of Tailscale, Wrapbook, and more are here to help you end your year on a high note.
It’s no secret that 2023 has been a tumultuous year for tech. But in some ways, for founders, it was a year like any other: navigating challenges and uncertainty to find opportunity and success.
Similar to our summer startup dish session, we asked a group of Canadian tech founders to reflect back on an unpredictable year. They shared their views on adopting new technologies, celebrated their biggest wins, and shared what learnings they’ll bring into 2024.
Meet the founders:
Saud Aziz
Co-founder,
Vault
Ali Javid
Co-founder & CEO,
Wrapbook
Avery Pennarun
Co-Founder & CEO, Tailscale
Fatima Zaidi
Founder & CEO,
Quill and CoHost
Benji Christie
Co-founder & CEO,
Formic AI
Michael Miller
Founder & CEO, Verto Health
In your opinion, what was the technology winner of 2023?
Several of our founders agreed with Vault co-founder Saud Aziz who said, “It’s hard not to say AI. The rate of advancement this year has really been impressive.”
Fatima Zaidi, founder of Quill, and Michael Millar, founder of Verto Health, specifically pointed out ChatGPT as an example of AI’s predominance in 2023, with Zaidi adding, “I think we’ve barely scratched the surface of the many different products and use cases that will utilize this technology.”
“AI will be a huge component in our 2024 roadmap but… we don’t want to just jump on the AI bandwagon.”
Fatima Zaidi,
Quill and CoHost
Zaidi anticipates that we’ll see a slew of products using AI in different ways in 2024. One of the ways her company, Quill, will use AI is to help clients derive meaningful insights and measure ROI from the podcasts they produce with the company.
Zaidi continued, “AI will be a huge component in our 2024 roadmap but… we don’t want to just jump on the AI bandwagon. It needs to be done in a way that will bring value to our users while also recognizing each client’s comfort level with the technology.”
Avery Pennarun, who founded Tailscale, a company that makes software for teams to connect on secure and private networks, thinks “supply chain security is one of the most important things happening in tech right now.”
“I’m a big fan of Chainguard,” Pennarun added. “They’re a software supply chain company helping make sure that your software project, which depends on probably hundreds or even thousands of open source projects, has some control over where its parts come from.”
How do you decide which new technologies to adopt and which ones to ignore?
Founders are often pulled in multiple directions when searching for scale, and it’s easy to fall prey to the belief that the quick adoption of technologies will help your company stay ahead, or at least not fall behind.
Ali Javid said he focuses on two questions when considering new technologies for his company, Wrapbook: “What is the customers’ problem? How do you most simply solve their needs in an enduring way?”
Similarly, Aziz (Vault) said he starts “with the customer and the ideal experience we want them to have. Working backwards from that experience, [we ask ourselves,] what do we need to build to deliver that experience and what technology will enable us to build it.”
Zaidi (Quill) and Millar (Verto Health) focus on ease of adoption and time savings.
“Technologies that give me back more than triple the time it takes to learn them are the ones I adopt,” said Millar. “The ones I keep using are the ones that give me back time and help me be closer to the person I strive to become.”
What’s one win in 2023 you want to celebrate?
Founders don’t celebrate their wins enough, so here are six wins worth taking into the New Year, with a reminder to share yours!
“This year we got serious about enterprise features needed to serve the largest customers that arrived through a self-serve funnel, and launched Tailscale Enterprise. It’s obvious there was pent-up demand. It’s been amazing how fast customers have responded.”
– Avery Pennarun, Tailscale
“I am so proud of how our teams have come together to solve audacious goals in creative ways. They acted in unison and nothing is more powerful than unity in action.”
– Ali Javid, Wrapbook
“We took our startup from the equivalent of an intense project to an actual ‘company.’ [We took] something that was a cool invention to something that we saw people really wanted/needed. Then [found] investors/employees who lined up with our mission and values to really accelerate what we were already working on.”
– Benji Christie, Formic AI
“In 2023, Quill launched our CoHost’s Prefix, the latest iteration of our podcast analytics tool which allows brands and podcasters to access in-depth demographic data and B2B insights, without switching hosting providers.”
– Fatima Zaidi, Quill and CoHost
“We were able to return back to our pre-pandemic vision and mission and secured three major contracts selling our enterprise Digital Twin, something we couldn’t during the pandemic.”
– Michael Millar, Verto Health
“Going from 0 to 1,500 customers in 9 months.”
– Saud Aziz, Vault
How many office dogs does your company have?
Meet Luna, Viking, and Charlie.
Admittedly, this question was a way to get our hands on cute puppy pics. But cats are welcome, too!
Zaidi (Quill) and Pennarun (Tailscale) both said having fully remote teams means office pets are always part of video calls. Pennarun shared: “One person here has a separate laptop their cat uses to join meetings so they can always be in focus. The cat gets more attention than I do, which is how it should be.”
Millar said the Verto Health office has so many dogs that the company runs a social event called Bark-in-the-Park.
BetaKit is waiting patiently for our invite…
How do you keep your team motivated during tough times? How do you keep yourself motivated?
A common trait that successful founders have is resiliency. But it doesn’t come without doing the work and setting healthy boundaries.
Benji Christie, founder of Formic AI, said he keeps himself motivated by making sure there is balance in his life. “Most times,” he said, “spending one hour with friends, cooking, or walking will make my next two hours of work more productive so I always make sure to find the balance.”
“A lot of companies aren’t going to make it. It’s scary.”
For his team, Christie takes an individualized approach, making sure he knows every team member and understands what keeps them going. “Once you have that understanding,” he added, “showing them you’re still right behind them and care about them really helps colleagues become a team.”
Zaidi, the founder of Quill, stays motivated by using her fear of failure as fuel. “Throughout my entire career, I’ve hustled to get to the next step. I’ve always been chasing the next goal, and given that I have the DNA of an entrepreneur, my insecurity and fear of failure are probably what motivates me. I hope I never feel like ‘I’ve made it,’ rather, I hope that the dream keeps evolving and keeps getting bigger,” she said.
Staying focused on the big picture is what keeps Aziz (Vault) and Pennarun (Tailscale) motivated.
“I share the same mission and customer obsession as our team. It’s been my driving force and we make sure all hires share the same,” Aziz said. “I’m very grateful to be in a position to have a meaningful impact on Canadians and it’s what keeps me motivated.”
At Tailscale, everyone is encouraged to focus on the big vision. “We’re not just another enterprise connectivity or VPN or Zero Trust company,” Pennarun said. “We’re all those things, but we believe everyone has the right to a fast, secure, peer-to-peer connection, even if it’s just between your phone and your Raspberry Pi at home. This vision of how we can ‘fix the Internet’ keeps everyone focused on the big picture instead of whether this month’s growth is a bit up or down.”
What’s one business problem on your mind right now?
Although inflation and interest rates have eased for now, the economy is still top of mind for many founders.
“The tech economy has to be the biggest thing on a lot of people’s minds,” said Pennarun. “Tailscale has been lucky, because the rapid rise of remote work means everybody needs newer and better tools to connect from home back to data centres and offices. But it makes fundraising harder, both for us and our competitors. We raised a very healthy Series B back in 2022 but it’s our responsibility to make that last as long as it needs to. A lot of companies aren’t going to make it. It’s scary.”
Christie, co-founder of Formic AI, has money on his mind as well. “There is both lots of money being spent in the world today (especially AI) while a lot of spending is being tightened up. I am trying to balance what budgets are going to stay versus dry up,” he said.
Javid wants to support the entertainment industry, which just survived a months-long strike that virtually halted production on film and TV sets. Javid wants Wrapbook, which makes payroll and accounting easier for the entertainment industry, “to support teams and industry as much as we can to be as prosperous as possible.”
Zaidi is focused on helping her team maintain a positive work culture as Quill commits to being a fully remote company.
“Quill has found great success being a fully remote company,” Zaidi said. “[But] running a fully remote company is not without its challenges. We work very hard to ensure our team is not working in silos and that everyone feels that our company culture is a priority… We want to always ensure that we are proactively working on things like collaboration and culture so we can continue to reap the benefits of our remote environment while ensuring our team stays motivated.”
Are you an inbox zero or 2,000 type of person?
This is an impressive group. Unlike the founders from our summer session (with one founder revealing his inbox sits at 100,000+!), more than half of our founders this time said they keep their inbox at zero or close to zero.
Please teach us your ways.
What’s one piece of advice that has helped you throughout your career?
“Always drill down to the core of a problem and really make sure you understand the why.”
– Saud Aziz, Vault
“Keep people smarter than you around you.”
– Benji Christie, Formic AI
“You can’t iterate around indifference. It’s better that someone hates your work than doesn’t react at all.”
– Fatima Zaidi, Quill and CoHost
Michael Millar of Verto Health has learned that there are some things that just can’t be outsourced. “As a startup CEO you will always be responsible for culture, strategy and making sure you don’t run out of cash,” he said.
What’s one thing you learned this year that you’ll bring into 2024?
Pennarun and his team at Tailscale learned a big lesson about how customers react to explicit messaging.
“We expanded our free plan to allow up to three users,” the Tailscale co-founder said. “But also put in some automated payment enforcement. The surprising thing to me was how many more [organizations] signed up two or three users rather than just one, just because we said it was okay. We weren’t enforcing it before, but almost everyone wants to be honest and comply with the stated limits. Relaxed enforcement is not as good as giving things away for free explicitly.”
Aziz (Vault) and Javid (Wrapbook) shared that their biggest learning in 2023 was connected to the importance of strong teams.
“The right team with the right focus can easily outperform teams 10X the size,” said Aziz.
“Providing clarity is the most powerful tool I and other people leaders have to improve velocity,” Javid continued. “To be great at this, we need to spend the time to think through the nuances, invite feedback from other people leaders, and create a culture where questions and debate is fostered.”
“This year has taught me that there are so many external forces that impact your business trajectory and there’s no point borrowing worry from the future and focusing on variables you cannot control,” Zaidi (Quill) said. “That is precious time spent away from pitching your customers, which is a big sunk opportunity cost.”
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