An interview with Owen Matthews: On culture, leadership, and why they matter more than revenue

I recently had the great opportunity to speak with Owen Matthews, a successful entrepreneur and investor based in Victoria, BC. Owen is the managing partner at the venture capital fund, Emend Vision Fund, which focuses on sustainability-enhancing and climate tech investments. He's also Chair of Alacrity Canada, a program designed to incubate and develop start-up technology companies. Owen is also a general partner at Wesley Clover International, another primarily tech-focused investment firm, located in Ottawa.

One of the reasons I wanted to interview Owen is that he has direct experience running a business and as an advisor to leaders. For example, back when he was an undergraduate computer science student at The University of Victoria, he started what would become a publicly listed company on the NASDAQ, that grew to over 100 employees, generated over $12M USD in revenue, and reached a market capitalization of $110M. Now as an investor at Emend, he's observed, evaluated and mentored hundreds of budding CEOs and Founders, as they try to emulate his success. So based on his well-rounded knowledge and multiple vantage points, I was curious to ask him about his views on leadership.

Another reason I was keenly interested to speak with him, was that I stumbled upon an interview he gave in 2016, and posted on the Alacrity website, in which he laid out his view that he considers culture a more influential predictor of a company's future success, than their 'revenue run rate.' (Revenue run rate is an estimate of a company's future annual revenue by extrapolating from recent revenue performance). This got my attention. Here was someone who stakes his reputation and the money of his investors on his ability to predict the future viability of businesses, and he's saying that intangible cultural factors are more influential than 'hard' financial data in his assessment process. So I wanted to know more about his thinking on that theme.

Here is a short outline of the contents of this newsletter article:

1. Full length interview with Owen Matthews (YouTube)
2. My key takeaways
   1. Agency
   2. Conversation and two-way dialogue
   3. Receptivity vs rigidity
   4. Shared leadership
   5. Safeguarding culture
   6. Select the right team that self-motivates
   7. The value of a high quality culture
   8. Characteristics of high-quality cultures
   9. Encourage quiet people to speak up
3. My favourite part of the interview (YouTube) (5 min clip + transcript)
4. Interview questions asked
5. Information on Owen Matthews and the organizations he's involved with
6. Trailer for 'The Brutalist' - a movie Owen co-executive produced, which won 3 Oscars!

Full-length interview with Owen Matthews (YouTube)

Here is the Youtube video to the full length interview with Owen.

Please see the notes embedded under the Youtube video, for a list of key topics covered, and timestamps for each:

(Recorded April 28/2025)

My key takeaways:

Here are some of the most memorable themes and learnings that emerged for me from the discussion:

Agency

Owen returned to the theme of agency several times in the interview. He values agency so much for a few reasons:

1. It’s motivating for team members. It’s energizing to feel accountability for your role, to possess the power to make decisions, and to use the full spectrum of your skills.
2. It fosters nimble decision making. According to Owen, command and control leadership, which discourages agency, “paralyzes decision making.” By contrast, those with agency don’t wait passively for the leader to tell them what to do. They act as needed.
3. It relieves pressure from the CEO. If the team acts with agency, the CEO doesn’t have to know the answer to every question and can rely on the intelligence and skills of their team.
4. It facilitates surfacing problems more quickly. Command-and-control leadership “cows” others into submission, and discourages them from bringing problems forward. Agency by contrast encourages team members to raise issues, problems, and growing risks immediately, so they can be addressed.
5. It helps keep small problems small. If team members with agency raise problems quickly, they can be solved before they metastasize into threatening or even existential crises. Another way I think about this is that agency encourages ‘preventive maintenance’ within the business.
6. It promotes learning from failure. If an agentic team surfaces problems right away, the entire company can more efficiently learn from those mistakes. So agency promotes knowledge acquisition. With command-and-control leadership that discourages agency, the team feels more reluctant to highlight mistakes or problems, and learning slows or stops altogether.
7. It enables the CEO to contribute more. Owen likens one part of the CEO role to a firefighter, who jumps into the fray to help resolve the most serious problems when they arise. However, if problems don’t surface due to a lack of agency in the team, the CEO can’t leverage their firefighting skills.
8. It creates a virtuous cycle of culture development. Owen suggests that if the CEO or senior leaders give agency to managers below them, those managers will in turn cascade that ethos to those at even lower levels. This cascading helps to engrain agency as a durable cultural principle within the organization.

Conversation and two-way dialogue

In the interview, Owen highlights in a subtle way how effective leaders need to stay in conversation and two-way dialogue with others. For example, he suggests that high agency team members feel empowered to speak up and start conversations, about problems in the business, which can lead to valuable learning conversations. Also, in the video clip excerpted below (see under heading ‘My favourite part of the interview’), he describes how the most successful leaders and teams he’s worked with all went to market with an idea, found out it was wrong, and had to refine it further to succeed. He suggested this refinement happens when leaders and teams stay in constant dialogue with external stakeholders who are in tune with the market, especially customers, who inform them about how the idea needs to change to solve the customer dilemma. By contrast he says that leaders who fail are often too wedded to their own idea, to proving that they're right, and they don’t listen well to new or countervailing information from the marketplace. Owen made a great point that the market is more powerful than ‘the idea’ underlying the venture, and so successful leaders find a way to tune into it’s signals.

Receptivity vs rigidity

This is another major thematic takeaway for me, which relates to the point above. The idea is that effective leaders are highly receptive to incoming information, and are not so rigid that they cling to their own ideology.

(Again see below under the heading ‘My favourite part of the interview' for a great 5 minute clip where Owen elaborates on this theme.)  

I think this is an interesting observation because 'leader receptivity' may not fit our stereotype of how an effective leader acts. You might assume that great leaders give directions more than listen and adjust their viewpoints, but Owen provides a nice challenge to this conventional thinking.

Shared leadership

After speaking with Owen, I reflected that his views on culture and leadership almost sounded like the goal was to hire such great talent so that you minimize the amount of time leaders need to spend supervising others. If you do this, you partly obviate the need for leadership, since everyone is motivated and acting with agency. Now I wouldn’t want to speak for Owen, and I assume he would still see a valuable role for CEOs/Founders related to strategic decision making and managing relations with investors, Board members, customers, and the market. But there’s an undeniable and subtle elegance to this idea – that is, that all members of the team share the responsibility of leading the enterprise. It moves the culture away from the notion of THE LEADER as the most important individual, and it flattens that status and power structure into something more shared and egalitarian, and signals that all members have valuable roles to play in the success of the venture. Owen hinted at this idea at certain moments, where he said “no one role is more important than the others” and suggested that he’s wary of CEOs/Founders that act too important, or close themselves off to others’ perspectives. 

Safeguarding culture

Owen talked about how it only takes one bad actor to ruin a culture.

(This jives with the views of Bob Sutton, Stanford University business school prof who wrote a series of books on incivility in the workplace, the first of which was memorably called The No Asshole Rule.)

Therefore, companies have to act quickly to address or remove these bad actors. If you wait too long, you're damaging your culture.

Owen gave the example of a company where 3/4 of the team strongly dislikes a leader, while the other 1/4 loves them. He described this as a narcissistic pattern, and suggested failing to address that person's impact on the culture, will further upset the already angry 3/4, and do a disservice to the somewhat deluded 1/4.

Select the right team that self-motivates

Owen makes the point that rather than leaders thinking about how they should challenge, push, or pull team members to higher levels of performance, he encourages selecting the right team members, who are already bursting with motivation, love their work, and are ready to make sacrifices for it. He suggested it may be futile to push someone to perform at a higher level, if they’re not intrinsically motivated to do so. He also added that if you hire high performance people, they will often introduce you to other high performers in their network. So they can be a rich reservoir of talent networks. It also strikes me that an advantage of this ‘pick the right people’ approach, is that it also frees the time of the CEO/Founder to focus on other critical tasks, other than trying to motivate their team.

The value of a high-quality culture

1. Great culture maximizes team motivation. Team members find it motivating to participate in a strong, healthy, functional culture.
2. Healthy culture contributes to organizational and operational efficiency. For example, a strong culture will generate high motivation, and a highly motivated team of 5 will outperform a moderately engaged team of 20. According to Owen, a "small and focused team" always outperforms larger less motivated ones.
3. High-quality culture enables a team to use their full spectrum of skills. The CEO/Founder only has so much time, ability, skills, intelligence – they can’t do it all themselves. It’s inefficient for them to make all the decisions, and to overcontrol every element of the business. A healthy culture creates agency, and empowers team members to perform their roles without constant oversight, using their full range of skills in their domain (e.g., sales, marketing, HR, etc.).

Characteristics of high-quality cultures

1. Agency, or shared/distributed/somewhat decentralized leadership.
2. A non-hero posture from the leader. This seems related to the agency characteristic mentioned above, and the more egalitarian style of leadership and culture that Owen values. This means the leader defers to their team. As Owen says “acting important is terrible,” and “you can learn from everybody.”
3. Respect, of others, of their ability to do their jobs, of the domains in which they're empowered to make decisions. Owen suggests respect binds team members together.
4. Effective communication, within the team, with information and conversation flowing easily.
5. Passion and energy.
6. Other indicators:
   1. How the most junior person is treated. This is a useful predictor for how management will treat new hires in the future.
   2. If someone isn’t fitting into the culture, or is being deviant in a way that could damage the culture, do people speak up about it? If so, that’s healthy – the fact that they can speak up, and that the CEO is receptive to that, are positive signs.

Encourage quiet people to speak up

On the themes of creating conversation, two-way dialogue, and healthy communication flow, Owen also described the importance of encouraging quiet people to speak up. He suggested that leaders need to be proactive in helping those quieter people find ways to contribute. He said that if leaders do this, they'll be more likely to garner a dissenting opinion, which is healthy.

This theme really caught my attention because I interviewed an executive a couple of years ago who told me that at one point in his career, he realized that he had ‘fast’ and ‘slow’ people in his team. The fast people wanted to debate key issues, in the moment, without prep, and tended to be more extraverted. ‘Slow’ people were still intelligent and had the ability to make impressive contributions, but they needed ‘soak time’ to organize their thoughts. So this leader realized that it was his responsibility to engineer team meetings about important topics, in a way that he first presented the key issue, but then asked people to think about it for 24-48 hrs before offering their feedback. He found that by doing this he could squeeze many more valuable ideas from those who needed more processing time. So Owen’s feedback here aligns with other practices I’ve seen work well for leaders.

My favourite part of the interview (YouTube + transcript)

I love this section of the interview because it highlights that leaders need to be highly receptive, flexible, and adaptable; to be in constant dialogue with those around them, whether they're internal or external to the company.

Owen suggests here that effective leaders, at least in early-stage ventures, are NOT command-and-control, they're NOT overly fixed on their own ideas, they're NOT obsessed with being right at all costs, they DON'T have to fulfill some kind of artificial hero-myth they read about in a book.

Rather they represent a less stereotypical version of a leader, one that's always listening and learning from those around them, who's highly open and receptive to their surroundings, and who has the humility to let go of a goal or idea when it's not fruitful and to pivot in a different direction.

Transcript from this short video:

Owen: I'll tell you what defeats culture, certainly in early-stage companies when you have - well one of the reasons I like early-stage companies is because you have the opportunity to set the culture. When I was hiring grads, we were teaching management from the very beginning [and so we were] able to build a strong culture from the beginning. It's much harder to reset a culture. But one of the things that really defeats cultures in early-stage companies [are] the myths around entrepreneurship. People read ‘the book’ about the successful entrepreneur, it was the brilliant idea, that was the moment that changed everything. And of course, it's written in hindsight by someone who's already very successful who, with ghost writers, wants to make a dramatic moment out of something. And the truth is the inspirational moment and the drive where “I was going to prove to the world that I was right” - that's terrible instincts for actually running a company. If I meet a CEO who has that myth in their head, like “my idea is the most important thing and I'm going to rail against the world and prove to everybody that I'm right…” And they're myths, they're not real, and they might be in the biography books but they're set up to be dramatic or to sound important or to make the successful person sound like they were brilliant in those moments. The truth is every company that we've ever been involved with that's been successful failed at what they were originally doing. So if I came across a CEO who was telling me “I'm going to tell everybody that I’m right and I'm going to push this on the market, it's going to work…” I actually have no interest in investing in them and I don't know any investor that would. Because it's a terrible person to work with. “I'm not going to listen to the market, I'm not going to listen to customers, I'm not going to listen to my investors, I'm going to show everybody that I'm right.” Well then you're going to fail, that's what's going to happen.

Tim: Too rigid, too dogmatic, not receptive to information coming in.

Owen: And every CEO, if they're not listening to the customer then they're not going to realize where the market opportunity is. Every company that we've been involved with that's successful, they went to market with an idea, and the idea was actually the least important thing. The most important thing was what's going on in the market. Is the market dynamic? Is there change going on? If you're in an established market, I don't know, banking in Canada, it’s really hard as a small company to break into an established market where there's no disruption going on. It's impossible. Whereas if you're in a good market where there's lots of disruption going on, there's lots of opportunity, there's a lot of money splashing around for opportunity, then what happens is you can go to the market with your idea and as you're working on it, you're going to learn a whole pile. So the other thing is your heart, you got to have the commitment. So as a team are you committed to make it work and you're going to stick together? [Now,] you've got the right culture, you're in the right market, there's a lot of money splashing around, there's high values, there's a lot of disruption, so there's an opportunity for a small player to get in, and you've got a great team with great culture who are listening and responding and can pay attention. And then you go to market with an idea and the idea is wrong and every company I've ever been involved with that's been successful, their first idea was wrong, it didn't work out. But they were paying attention, they got lots of feedback, they were actually talking to customers and trying to solve a problem. And when it didn't work, they learned enough that another door opened, and it was a bigger and better door anyway. So if I was to tell you my idea is what's important because I read the book and that's what entrepreneurs are supposed to do and I'm so passionate that I'm going to prove to you that this idea is correct - well given my experience that’s definitely going to fail as opposed to someone who is open [to] recognizing that the market is shifting, recognizing that there's an opportunity… So that concept of “I'm right and I'm going to prove to you that I'm right” - and that filters down [to] how management operates - is terrible for culture, it's terrible for the strategy of the company, and it's taken from a myth which are books written in hindsight by people who are who are already successful who are trying to make dramatic moments in their history sound exciting. The truth is it's not at all that exciting, it's hammering away at a market and understanding what's going on with your customers that leads you to your biggest opportunities. 

Interview questions asked

Here's is a list of the questions I asked Owen:

Owen's story

1. Over the course of your career, you’ve been an entrepreneur, venture capitalist, investor, and teacher/mentor to many young leaders building businesses. I’ve given a bit of background just now, but could you describe your career journey in your own words, as well as some of the big milestones you’ve experienced along the way?

Culture

1. One reason I was interested to speak with you was because I read an interview you posted on the Alacrity Canada website, back in 2016, which caught my attention. In it you mentioned how you value the culture of a company more heavily than its financials, when judging its prospects. Can I briefly read the passage that sparked my desire to speak with you? Here it is...

Culture is always the most important thing. Is the team willing to change their minds if it’s in the best interest of the company, or are they most concerned about self-interest? Are they working hard because they’re dedicated and passionate about what they’re doing? At its core, the details of the company are less interesting to me than the approach of the people who are in that company. How people in the company are treated is more telling to me than the revenue run rate. I’ve seen good revenue run rate businesses evaporate because they lose their culture as they grow. If the culture is wrong, great team members don’t feel appreciated and either leave, or are unduly limited in their contributions. So I look at culture first and foremost.

...Can you tell me more about what makes you value culture so much when evaluating the prospects of a business?

3. What kinds of cultural characteristics do you look for in a business?
4. Young, fast growing companies are highly dynamic, and I imagine personnel changes frequently. How do you judge whether a company’s positive culture will be durable over time, as the company changes? Or do you just assume culture will evolve over time, and you find ways to help founders and CEOs just manage that evolution?

Leadership

5. In your experience, and based on the many companies and CEO’s you’ve observed over the years, how should leaders build strong cultures that support business success?
6. I’m really interested in the question of how leaders can challenge, push, and pull their teams to the limit of performance, to the absolute peak, but in sustainable ways, that preserve motivation, relationships, and culture within the team. As someone who is trying to create high-performance companies, how do you think leaders can challenge their teams to the limit, while balancing that with maintaining healthy relationships, motivation, and culture?

Career influences

7. Finally, in your career story, I noticed that you worked with your father who was himself a successful businessman. This caught my eye because I also had the benefit of being mentored by my father. What did you learn from him that has helped you become successful? Also othan your father, who else has influenced you, and helped shape your thinking on business, entrepreneurship, and investing?

Information on Owen Matthews and the organizations he's involved with:

Emend Vision Fund

Alacrity Global, Canada, UK

Wesley Clover International

Trailer for 'The Brutalist'

Check out the trailer for this movie which Owen was an executive producer for... it was nominated for 10 Oscars, and won 3!

Tim Jackson, Ph.D. provides advisory and deep expertise on executive leadership development, to dynamic and high performance organizations.

Tim's services include in-depth executive assessment using interviews and gold-standard qualitative data analysis techniques; executive coaching rooted in his deep expertise of the drivers of leadership effectiveness; workshops built with evidence-based data and models that transfer high-quality knowledge, and enhance the impact of participants; and facilitated sessions that create dialogue and conversation among senior leaders, in a safe environment that promotes shared learning.

Throughout his 18-year career, Tim has worked with a wide variety of clients, including CEOs, executives, managers, and individual contributors; leaders located in Canada, the US, Europe, and China; individuals spanning 11 different industry sectors and every key functional area; and those driving major change inside private-equity owned businesses.

The following are examples of how Tim has delivered value to his clients: he assessed and coached 28 leaders in a large Canadian CPG company over a 5 year period, including preparing high potentials for promotion and helping derailing leaders course correct; he coached senior leadership team members and middle managers in a global chemical company to navigate dynamic change resulting from the largest acquisition in their history; and he provided assessment, coaching and advisory support to the CEO of a Canadian ‘supercluster,’ a federally-funded accelerator of strategic economic activity (this cluster received renewed funding in early 2023).

Tim has published his ideas about leadership in various outlets, including The Globe and Mail, Forbes.com, several HR trade magazines, and peer-reviewed journals. He also writes original articles about leadership topics in his newsletter at www.timjacksonphd.com. He has also shared details of his practice at leading conferences like the Society for Industrial and Organizational Psychology.

Tim also engages in regular professional development to enhance his practice. He is certified to administer and interpret Hogan Assessments (HPI, HDS, and MVPI). He has also completed multiple courses on qualitative research methods, to enhance his interview-based 360 process. Also, to build his knowledge about leadership best practices, he undertook a multi-year project to explore how leaders can challenge team members to the limit of performance, but in a sustainable way. This project involved 37 interviews with executives from VP to CEO levels.

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3. Workshops: Tim offers two customized workshops for executive audiences. The first is titled 'How leaders can challenge, push, and pull teams to the limit of performance, without breaking them.' This content is based on Tim's original research, using data from 37 executive interviews. The second workshop is titled 'Foundational leadership concepts for new executives,' and summarizes all the key drivers and derailers of leadership effectiveness that Tim has learned about in his 18 year career, distilled from both academic sources and practical experience.
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Please feel free to contact Tim with your feedback about this site, questions about his services, or to share your own ideas about leadership in organizations.

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