Hunter Walk: So why venture capital, why early stage, and why Canada?
Chris Neumann: I’ve been lucky to have been a part of 5 startups going back to the late-90s, including two that were VC-backed (DataHero and Aster Data). After DataHero was acquired, I felt like it was time to try something new. 500 Startups was looking to add someone with an enterprise background to their investing team, so I made the leap into venture at the start of 2017.
At 500, I had the opportunity to work with early-stage founders from around the world and quickly realized that this was where I wanted to spend my time. I really enjoy the creativity and problem-solving that takes place during the early stages of a company, when founders are trying to solve a crazy number of challenges in parallel in order to get to product-market fit.
As to “why Canada?”, I’ve spent a lot of time in international ecosystems over the years (I’ve invested in startups in more than 20 countries and helped run accelerators on 5 continents). That exposure gave me insight into the significant knowledge gap that exists between Silicon Valley and the rest of the world. When you spend most of your time in the Bay Area, you’re oblivious to how much of a global outlier the region really is in terms of the density of experience and availability of people who have “been there before”. I felt that there was an immense opportunity to help narrow that gap for international founders, which led me first to found Commonwealth Ventures and eventually to move back to Canada and join Panache Ventures.
In the last 5 years, the Canadian tech ecosystem reached a significant inflection point in terms of the frequency with which world class startups were being founded and the ability of the ecosystem to support the creation of globally-impactful tech companies at scale. Toronto has now firmly established itself as the third largest tech/startup ecosystem in North America (sorry Miami) while Vancouver has finally embraced its proximity to Silicon Valley and the advantages that come from being the only major international city in the same time zone as San Francisco. What’s happening in Canada right now from coast-to-coast-to-coast is really quite remarkable.
CN: Thanks so much – that means a lot coming from you.
Speaking to international founders – which is really my focus – the number one piece of advice I would give is to spend time in the Bay Area. And I don’t mean going for a vacation or one of those week-long “startup tourism” trips, but really spend time there. Like a month or two.
The corollary to my earlier comment on Silicon Valley’s outlier status is that many people who live outside of the U.S. downplay or outright dismiss the advantages of being in the Bay Area, without really understanding them. They latch on to the narrative that “great companies can be built anywhere” and assume that founders around the world are competing on a level playing field, when they couldn’t be further from the truth. It’s a mix of naivety and nationalism that is detrimental to the success of both the individual companies and the broader ecosystems.
HW: Of the companies you’ve backed that truly failed financially (let’s define that as weren’t able to return the invested capital back), what percentage of those CEOs would you back again? What are some differences between those you would line up again to support and those you merely wish best of luck to?
CN: That’s a great question. I’d have to say that number is probably less than 10%.
For me, there are three major differences between CEOs I would back again and those I would not:
First and foremost, how capable were they as CEOs? In many cases, it becomes apparent over time that a particular founder isn’t actually well-suited to the role of CEO. Maybe they can’t sell. Maybe they’re too stubborn and their own idea gets in the way of hearing the market’s feedback. Maybe they have trouble letting go of things and empowering others as the team grows. Being the CEO of a company is a singularly unique role with demanding expectations and responsibilities, and most people really don’t belong in that role.
Finally, are they able to thoughtfully reflect on and learn from their failures? Once the dust has settled and the CEO has had time to process the emotions that come with having your startup fail, can they look back objectively and identify things that they might have done differently or decisions they made that turned out to have negative long-term consequences? That’s a big one for me.
It also goes without saying that how a CEO handles themselves in the final days and weeks of a company plays a crucial part in how investors ultimately see their legacy. You’ll never be able to tie everything up with a bow, but acting ethically and with integrity while trying to take care of your team is ultimately what matters.
HW: What’s the dumbest argument that our industry is currently having and why is it “remote vs hybrid/in-person?” But seriously, you’ve been a founder/CEO – what choices did you make about the culture of your startup that you think suited you well, and which ones would you revisit (or try to do differently)?
CN: If I never again have to read a bunch of entitled tech bros mansplaining on twitter about their way of working is the only way, I will die a happy man.
When we founded DataHero back in 2011, there was a trend going on where people were obsessively trying to “design” their company cultures. I never understood that – how on earth you could reason from first principles about culture and simply proclaim “this is what it will be” (Later, when Ben Horowitz published his book “What You Do is Who You Are,” I realized that I wasn’t the only one). Overall, we just tried to do the right thing. Treat people well. Show them that you respect and appreciate them. But also make sure everyone understands that startups are hard and work ethic is important – so keep the bar high.
In terms of specific choices, I think we did a really good job of being pragmatic. We didn’t overthink things. For example, we had a hybrid work schedule starting in 2012. M/W/F in the office. T/Th work from home. Why? Because Bay Area traffic sucked. That’s it. That simple.
We also worked really hard to keep a pulse on how people were feeling and take breaks when needed. For example, I remember one period where the whole company had been grinding for a couple of weeks leading up to a big release. It was apparent that everyone on the team was getting really stressed, so one day we declared that we were closing the office at lunch and going to get massages. We then took the entire team down the street to a Thai massage place, paid for everyone to get one, and went out for beers afterwards.
I think the hardest choices for me were around people who were underperforming. It’s easy to proclaim that you’re going to “hire slow and fire fast,” but when it comes down to it, very few people do that effectively – especially in resource-constrained startups. I can think of a few cases where I kept underperformers far longer than I should have, leading to longer-term cultural issues amongst the rest of the team.
HW: Who’s an investor you consider to be a role model and why?
CN: There are so many investors I’ve had the privilege of learning from over the years. Josh Kopelman was an early investor in Aster Data and for me really exemplified what it means to be generous with your time as an investor and show respect for founders. When Aster Data was acquired and I left to found DataHero, he spent more hours than I can remember meeting with me and brainstorming about the potential for cloud BI. On the one hand, he was definitely playing the long game and hoping for a potential investment, but it was more than that. Even after passing on our Pre-Seed round, he continued to make time. It was only later that I realized how much of an outlier he was in the way he interacted with founders.
From a partnership standpoint, the guys at Foundry (who ultimately led our Pre-Seed round) have been another role model for me. They make a point of encouraging founders to reach out to any of the partners – and have no ego around that. When I was a founder, it was such a powerful way of supporting portfolio companies. Now that I’m an investor, I can see how much efficiency and effectiveness comes from trusting your partners – not only when it comes to deferring on “risky” investment decisions, but also in terms of handing over a bit of “control” of the relationship with portfolio founders. There are a lot of things they do from a portfolio support perspective that we’ve looked to as examples at Panache.