The first rule of real estate

Before you read this, go read Mark MacLeod’s post on Who not to take money from…. It’s not related to this post, but a great post for entrepreneurs to read when talking about investors.

RT @Cmdr_Hadfield Chris Hadfield 19 Jan With a long tradition of hockey on the shore of Lake Ontario, introducing Toronto - Go Leafs Go! @MapleLeafs

If geography doesn’t matter, than why do plane tickets cost so much?

“When it comes to raising funds, I just don’t think the geography matters that much. Good solid product that solves an actual pain can find it’s way to investors any where in the world thanks to the internet.” – Adeel vanthaliwala

I read a lot of comments like Adeel’s. And I agree that geography might not be the most meaningful filter, it still impacts startups in raising capital. It is far easier to raise money from a broader range of sources today, than it was 10 years ago. Changes to Canadian Tax Act (Section 116) have helped open the border to outside capital. There has also been a rise of new Canadian funds that have all closed in the past 2-3 years including: OMERS Ventures, Relay Ventures, Rho Canada, BDC Venture Capital, Real Ventures, Version One Ventures, Golden Venture Partners, Tandem Expansion Fund , Georgian Partners, etc. I worry that comments don’t take into consideration the complexity and challenges of raising capital. The impact of geography on raising capital has been reduced, but geography does still affect startups raising money.


The best advice on geography is from Brad Feld in 2007:

  1. Don’t worry about it
  2. Be realistic about the available resources
  3. Find the local entrepreneurial ecosystem – now!
  4. Don’t try to get investors to do unnatural acts
  5. Don’t play the “we can be virtual” game

From the point of the investor, geography probably doesn’t matter that much. Unless of course there is a limitation in the partnership agreement that limits the geography where the capital can be invested. There are other more practical concerns about having remote startups including legal and or taxation concerns (see Section 116). Or the ability for a startup to leverage personal/professional networks for hiring, business development, etc. And none of this describes the challenges of having to spend 6 hours flying each direction to attend a board meeting. But beyond that, proximity is not a requirement from the investor side. Good startups can be located anywhere.

“Local brewers = geography matters. As macrobrew VCs are increasingly spending time in multiple geographies (separate from their HQs) there is real potential to differentiate along knowing that you can actually sit down and see your VC face to face. For some that’s important, but for some that’s a negative. Just as some people here in Boston prefer drinking Cambridge Brewing Company ale; others could care less it was brewed locally.” – David Beisel

I like David Beisel’s   model of the VC industry starting to become more similar to the beer industry. There are larger funds, local funds, specialized funds, and individual partners. They all matter differently to entrepreneurs depending on the company, stage of development, location, etc. Understanding the available resources and your ability to access them are key.

Traction trumps geography

Non Linear Growth

There is going to be the inevitable argument about companies raising money from foreign VCs. The great news is since the changes to the Tax Act and the fall of Section 116, we have a lot of examples:

Not to belabour the point, it is possible to raise capital from foreign investors in Canada. But the level of traction demonstrated by most of these companies was very high. For example:

“Since HootSuite’s Series A financing, we’ve grown from 200,000 users to almost 2.5 million! We’re proud of our progress and are looking forward to the future with more success on the roadmap.” – Andy Au, Hootsuite

According to my calculation that’s a 431,690% CAGR of the registered users between when they announced their Series A and Series B financing. Go big or stay home. Traction and growth trump geography. Paying customers, a scaleable business. Being able to demonstrate that for every dollar that goes into the business you understand how many (more) dollars come out. You need to be able to demonstrate appropriate milestones to mitigate risk.

Avoiding Unnatural Acts

“Don’t try to get investors to do unnatural acts: Assuming you are looking for capital, focus your energy on two categories: (1) local investors – either angel or VCs and (2) VCs that are interested in the specific business you are creating. In category #2, “software” is not a specific business – you need to be a lot more granular than that. Your chance of #2 is enhanced by a relationship / investment with someone in category #1, so make sure you focus enough energy on that early on.” – Brad Feld

The secret here is that social proof that VCs are doing deals north of the border is not enough on its own. You need to focus your efforts, and assuming that you’re doing everything you can to hit accretive milestones you still need or want to try to avoid doing unnatural things. A local investor is not required, but it can be a signalling risk about the team, market, product, or other, i.e., what am I missing if local investors are cold? (There are situations where you can imagine an entrepreneur choosing to avoid local investors, particularly if they have had a deal go sour in the past, but usually the entrepreneur discloses this very early).

What to do about location?

  1. Fugetaboutit!
  2. Start nailing concrete milestones that demonstrate traction and mitigate the risk associated with your business.
  3. Get connected to your local community. Look for events like Founders & Funders, Elevator Tour or GrowTalks to have initiate low risk conversations with both local investors and entrepreneurs that have raised capital.
  4. Do your research! Use AngelList, Google, Bing, LinkedIn, portfolio pages, etc.  to find partners following and investing in companies in your very specific vertical.
  5. Figure out who locally is investing locally and figure out how to get a warm introduction and find 30 minutes to meet.
  6. Listen, ask questions, try to figure out what is missing, what is the biggest risk factor and how you might mitigate the risk.
  7. Rinse and repeat with non-local investors aka get your ass on a plane and keep hustlin’ (go re-read Mark Suster’s Never ask a Busy Person to Lunch).

The White North – It’s Great for Seed-Stage Startups

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Sit down with any Canadian entrepreneur and you’ll often hear similar grievances about the Canadian startup community. The consensus seems to be, “It’s getting significantly better, but we’re risk-averse, funding is hard to come by, and the US is a bigger market.” We are a a startup that decided to move from Silicon Valley (as part of the Y Combinator Summer 2012 cohort) to Toronto. We’ve seen a wider  range of startups and startup hubs than most. We’ve been able to compare and contrast the communities, and have a lot of faith in the Canadian startup scene as a whole. We want to share why.

As Canadians, it’s easy to look South and feel overwhelmed. The United States is ten times bigger in terms of economy and population. It’s difficult to fault an ambitious entrepreneur for wanting to move South and capture a significant chunk of a significant market. Likewise, no maturing startup can avoid the US as a potential market…

The question for us was: what are the pros and cons of being a seed-stage startup in Toronto, or Canada as a whole?

Why Toronto? And Why Now?

Seed-stage startups rejoice — the Toronto/Waterloo community is a great place for seed-stage startups. Before I begin listing the benefits, I do want to iterate that it’s all one big place [Ed.: Can’t disagree here, when you fly in to SFO or SJC, it’s still the Bay area]. At times, it seems unfortunate to me that Toronto and Waterloo are treated as two separate entities in which a startup would operate. Sure, driving down Highway 401 isn’t the most enjoyable experience, but your startup will face bigger challenges than congestion during rush hour.

1. Talent Pools

The universities spanning the Greater Toronto Area and surrounding cities boast over 200,000 undergraduate students, many of which are studying engineering, computer science, or other technical fields. The Universities of Waterloo and Toronto both boast high quality math, computer science, and engineering departments, many of which are regularly hounded by big and small companies for potential recruits.

Hiring was a key factor for us when choosing our base of operations. Being able to pick from so many students, let alone professionals and developers working for large corporations, helped make this an easy choice. Better still, few startups actively approach this population — most of the keen, startup-oriented folks end up traveling to San Francisco to look for jobs. By bringing the opportunity to their doorsteps, we made the sometimes frightening decision of jumping into a startup significantly easier. Our recruits get all the joys of working for a Silicon Valley-funded startup without the hassle of immigration, relocation, and saying “goodbye” to towns they know and love.

2. Excited Customers

Few people realize that Toronto was the first city in North America to surpass 1 million Facebook users. Move over New York, and see you later, San Francisco! Not only are Canadians notoriously friendly (collecting feedback on your product will be easy!), they are also hungry and interested in innovative products. Others have argued that Canadian cities are good grounds for experimentation as well, citing the fact that we tend to focus on stable techological trends and avoid fads that might only survive in more stereotypically tech-crazy startup hubs.

While I wouldn’t go so far as to cite this as a reason for basing your startup in Toronto, it means that you don’t risk finding a product-market fit by being based here. Combined with our own strong network and following here, it was a safe bet for us to settle down and start experimenting with an initial set of corporate customers or pilots.

3. Low Cost of Operations

Compare your average salary, apartment rental, and parking spot in Toronto to those of US startup hubs like Silicon Valley or New York, and you’ll see a noticeable difference in pricing. The Toronto/Waterloo area enjoys a significantly lower cost of living than many other hubs, which often means that your own expenditures will be significantly lower — if you’ve already raised angel or seed funding, this essentially boils down to a longer runway for your company.

Pair the low cost of living with Canada’s many government-supported startup programs, and your cost of developing a product can be 40% of what it would cost in the US. Better still, basing your operations in Toronto/Waterloo mean you have a 90-minute flight to major American cities, which could easily become your next point of contact or expansion for your products. All the benefits of a large global city, and few of the costs!

4. A Changing Startup Landscape

Startup entrepreneurs are often goaded by their investors to ride waves of industrial changes and take advantage of major societal shifts. A quick look at AngelList valuations by city and startup hub shows startups in Toronto/Waterloo are holding their own, on a global scale. Our own seed-stage round had investors from both sides of the border, and many regularly told us they see Canada as a great opportunity to expand their market reach outside Silicon Valley (or the US as a whole).

As more Canadian companies have fantastic and successful exists — think Radian6, Eloqua, or BufferBox — we’ll see more investor interest in our region. If you’re an entrepeneur keen on surfing an investor wave, getting ready for what interest might come to Toronto is a great place to start.

Planning Ahead

As with any discussion on the benefits of a major and complex decision such as base of operations, one should not forget what they do give up by being based here. It’s important to plan ahead, and any startup choosing a base of operations in Toronto, particularly when planning to expand to the US, should plan around this.

1. Don’t forget your friends down South

It’s easy to limit yourself to your geography. Remember that expanding into a city or market in the US means you first need to develop a network there. Are you planning to raise a VC round in three months? Planning to expand from Toronto to the New York City market in six? Start building those networks now. It is amazing (or gloriously terrifying!) how important serendipity is to the success of some startups. Ensure you have a network in these cities, even if the connections are only digital.

In our case, we keep in touch by attending conferences on a regular basis, maintaining e-mail contact with the companies and VCs we admire, and constantly ask ourselves if it’s time for an in-person visit.

2. Use Global Benchmarks

One of the most important things a startup can do is to do is benchmark itself against its industry, or other startups. Know what valuations your competitors are getting, and what sorts of employees they are hiring. Most importantly, ensure you’re using global benchmarks. While being the best “Canadian” startup is nice, remember that to truly achieve global scale, you’re competing against the best startups in the US, China, Israel, and everywhere else. It’s easy to become complacent by forgetting about these massive centers of innovation.

Indeed, one of the biggest benefits of our being in the Y Combinator program has been seeing how our batchmates work, move quickly, and succeed at nearly any cost. Seeing this hunger and drive has left us with no excuse for avoiding success. We use our network of VCs, friends around the world, and startups we admire as a way to regularly benchmark ourselves and ensure we’re progressing at a decent pace. Case in point: the Big Data industry is growing over 40% every year — and we aim to outperform it.

3. Pay It Forward

And please, remember to pay it forward. If you choose to grow, develop, and succeed in these fine, frigid cities of ours, ensure you give back to the communities. As Brad Feld so eloquently wrote in “Startup Communities”, the only way to make a startup hub successful and grow is through having entrepreneurs leading the community, to have them involved for the long run, and to be inclusive.

Sometimes that’s easier said than done, as evidenced by Zak Homuth’s view on Toronto startups in the Startup Genome: “We have all been somewhere else, worked somewhere else, and got money somewhere else.” Success breeds success, and it is important that for those of us who grow and succeed through the benefits of our community also give back to it.

To us, building a successful community is as rewarding as building a successful startup. We aim to ensure that every single person passing through or working with Canopy Labs will leave with better career prospects, more ambition, and the necessary training to succeed in whatever they do. Not only does this make it easier to hire great, talented individuals, it also ensures we’re constantly developing as a team.


While the Toronto startup community is getting more attention in recent times, there is still a great deal of work to be done. Toronto is a fantastic place for startups and Canopy Labs is a case in point. We’re a six person startup with a significant runway and exciting customers, and all of this is enabled by our being in Toronto. At the same time, we’ve got a global mindset: we benchmark ourselves against all players in our industry, and are constantly building and growing our networks in new cities and countries.

We’re proudly Canadian, comfortably Toronto-based, and our office is on Richmond / Spadina in the heart of Toronto’s startup hub. We’re excited and happy to be here, and feel we’re growing faster here than we could hope to grow anywhere else. Drop by any time!

Firing People

I hate firing people. It’s the worst part of my job. Even after all these years I still spend days or even weeks agonizing over a decision to let someone go. I feel absurd complaining about this, given that of course it’s a hundred times worse for the person being fired than it is for me. Still, I hate firing people.

My first firing at Top Hat was our VP Sales. He was employee number two, he joined right after we raised our angel round. In retrospect it was doomed from the start, and it was entirely my fault. I had no idea what I was doing when it came to building a sales organization and brought him into a role that didn’t make sense (read about the lessons learned in building a sales team). It took me 6 months before I finally pulled the trigger. In the end, it was undoubtedly the right decision and set the company back on track. But at the time it was an extremely tough call. It was admitting failure – to myself and to our investors – that this first major hire was a mistake. I felt  ashamed about it for months and kept convincing and re-convincing myself that we could still make it work.

As a general rule once you’ve lost faith in an employee, things rarely get better. You can sometimes fix a skill-level problem by giving someone time to grow, but you can never fix a personality problem. If you’ve identified that someone isn’t a fit you need to move on it quickly and decisively. The longer you wait the worse it will be for both parties.

Firing is an essential part of running a successful company.

In a narrow way, it’s actually more important than hiring. You could, in theory, use a shit-against-the-wall style hiring strategy and as long as you filter out the bad apples quickly enough you’ll be able to build up a functional team over time. Of course that’s probably not the best approach.

The reality is that even the most effective interviewers are rarely more than 70% or 80% accurate. The average interviewer is quite a bit worse than that and isn’t much better than chance – often even worse, because the naive approach just selects people who are great in interviews, which disproportionately selects for bullshitters. However, even if you’re some kind of super-human talent screening machine with a 95% success rate, that 5% will accumulate and degrade the culture until you’re surrounded by bozos.

The Best Firing Process is a Better Hiring Process

Of course the best “firing process” is not to have to fire people, which can only be done through effective hiring. That being said, not having an effective firing process is like not having an immune system – the first cold will eventually kill you.

It’s fairly common knowledge these days that A players only like to work with other A players. A slightly more subtle observation is that someone’s status as an A player isn’t fixed. Bringing a weak player onto a team has a tendency to poison the culture and downgrade the rest of the team (especially if that weak player has a shitty attitude.) This bad apple syndrome has been observed to happen fairly reliably in studies on organizational dynamics.

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The Bad Apple Syndrome

We’ve experience this at Top Hat a couple of times. One of the most instructive was with our inside sales team. Early on when we were in a pinch to fill the team we lowered our standards and brought on a few people that we should have passed on. The results were disastrous. The quality of the team degraded and eventually hurt not only the inside team but also other parts of the company that came into contact with it. It took nearly a year of solid effort to rebuild the team. For a time it seemed hopeless. No matter what changes we put in place, no matter how much talent we threw at the team, the cancer of negativity and poor morale just wouldn’t go away. The most profound mistake we made in the process of trying to fix the team was to keep those who were performing well but had a negative attitude.

There was a pattern we observed a few times: we’d put a new person into the team, their performance would be great and they’d be super enthusiastic. Then like clockwork after a week or two their numbers would slowly drop, and they’d become engrossed in the culture of negativity and gossip. It was only after the cleared out the ringleaders who were perpetuating the negativity (who happened to have decent performance numbers!) and put in strong positive management that things finally began to change. The most amazing thing is that many of the people who were B or even C players when the team was dominated by negativity shot up to solid A player status. The overall output of the team per person went up by nearly 300%. In addition it seems as though life was trying to setup a lab experiment for us to prove just how much things had improved – we had a person who had left the company a few months prior re-join the team. His feedback was that he was blow away, he couldn’t believe it was the same team.

Lessons Learned

The first lesson we learned was that no matter how strapped for manpower you are, no matter how much it seems like the world will end if you don’t fill a position, compromising on the quality of talent will surely be more damaging. Second, we learned that in fixing a damaged team the key is to identify the cultural sources of the underlying problem and focus on those. Finally, we learned to use a divide and conquer approach – we would pull all the top talent into a separate team while rehabilitating the broken remaining team separately – it really helped prevent the “negativity cancer” from spreading while we were fixing things. These are simple things in retrospect, but it took a while to pull it off.

One of the most revealing questions I tend to ask when interviewing potential managers is whether they’ve ever had to make the decision to fire someone. The answer and subsequent discussion usually tells you two things: first, it tells you if the person has ever had to deal with the most difficult problems in management, second it tells you if they know how to handle those problems through the process they followed. Assuming the person has ever had to hire and manage a team of a decent size for any length of time, it’s almost certain they’ve made hiring mistakes, and their answer tells you that they know how to detect and correct these mistakes. If the person simply walked into a mature team, or has had HR handle all the hiring/firing decisions for them, then they’ve been living on easy street.

The process of firing someone is always somewhat unique to each situation. That being said there are some basic principles that you should always follow:

  1. Give people plenty of notice and regular feedback. Give people several chances to improve. The actual firing should never be a surprise – if it is then you almost certainly did something wrong in setting expectations. Depending on the role the whole process should take 1-2 months (longer for senior roles.)
  2. Try to be generous with severance and leave the person in a good spot to find their next employment. I know it’s not always possible in a startup, but do what you can. It’s the decent thing to do.
  3. Take time to reassure the rest of the team and explain (with discretion) the process that was followed and why the decision was made. Letting someone go is always a huge morale hit (even if the person wasn’t well liked, it still scares people.) You need to make people understand that their job is not in danger.

Firing someone is always a brutal experience. Anyone who says otherwise is either lying or is a psychopath. That being said, it’s unfortunately a necessary evil and understanding when and why it needs to be done is essential to the success of any business.