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How Can Angels Structure Their Portfolios Better?


[Note: this blog post also appears on the NACO Canada guest blog by Randall Howard]

Angel portfolio management remains surprisingly primitive. Many Angels have built up substantial portfolios over time, yet few give much thought to ongoing management of these valuable assets. The many various spreadsheets, documents, share certificates, warrants, emails and other essential documents are often scattered far and wide. I understand first hand the challenges Angel investors face when managing their portfolios and I also understand that things need to change.

At the beginning of October, I will be moderating a panel at the 2015 National Angel Summit, regarding best practices in portfolio structuring management and succession planning in order to build awareness, and activate change, around this issue. The panel will include two “Super Angels” and a Family Office Professional who will provide first hand perspectives on approaches to filling the portfolio management gap.

The fundamental question we will be addressing is, “how can Angels structure their portfolios better?” We will also be diving into the importance of succession planning for Angel investors.

It may sound morbid, but how many Angel investors have planned or even thought about the huge challenges they would leave their loved ones and executors when they die? Angel investors need to have a well-executed plan in place for their portfolio companies. Like inside companies, succession planning is all about planning for the inevitable to lessen the burden for those who follow.

With this panel, my hope is to shine a light on these less mainstream topics, through awareness and conversation. Throughout the 55-minute session, Summit attendees will learn tangible strategies and tips for proper portfolio management and succession planning. The panel will also ensure that as many audience questions are answered as possible.

It should be noted that the Summit is the signature event of the Canadian Angel investment community, and this three-day conference is an excellent chance to network with startup CEO’s, attend panels and workshops, sharpen your skills, learn from industry leaders and more.

Register for the 2015 NACO Summit to join this discussion.

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aca-summit-2015 512x250In mid-April, I attended the 10th annual ACA Summit hosted by Angel Capital Association in San Diego. With about 600 people in attendance from dozens of countries, it was an excellent chance to get tuned into the latest trends happening in angel world at large.

And since Angel Investing is now a global phenomenon, it is interesting to note that ACA Summit can have two faces. On one hand, it is a very international gathering of Angel investors and yet sometimes the content reflects the fact that ACA is primarily an association of US Angel investors, for example by showing trends without regard that Canadian angels are just across the border.

The international range of attendees was striking, with many delegations from various European countries; Latin American countries like Mexico, Chile and Barbados; India; a particular concentration from Australia and New Zealand and of course Canada. Regarding this antipodean concentration, one attendee found it odd that there were more of participants from halfway around the world than from Canada.

I am a member of the program committee for Canada’s own 2015 NACO Summit which is being held October 6-8 in Niagara-on-the-Lake, Ontario, right on the US frontier. I see a huge opportunity to learn and connect with more US and global angels.

Each year, the Angel Resource Institute publishes statistical information and trends in US Angel investing and at ACA released their 2014 Halo Report.

I’ve chosen some personally curated highlights both of that report and the overall conference:

  • Overall US Angel investment was about US$25 billion in 2014, surpassing venture capital investments. This represents over 300,000 investors in over 70,000 deals. We continue to have less comprehensive data for Canada, but we still lag on a per capita basis, but the gap is narrowing.
  • Although Crowdfunding was a major topic of discussion, it is still less than 2% of the above $25 billion figure, definitely lagging places like the UK where it is already at 5%.
  • Median deal size grew over 10% to $2 million in 2014, when co-investment is included. Median pre-money valuation grew 20% to $3 million.
  • The largest region for  deal dollars (17.2%) was the Great Lakes Region (from Wisconsin to Ohio), surprising to those who thought most deals happen in California. Further, almost 50% of all deals are in states on the Canadian border, clearly presenting cross-border syndication opportunities.
  • Perhaps because of high valuations in the tech “hot spots”, such as New York City and California, more syndication across greater distances was reported, which goes against the traditional notion of investors focusing within a one-hour drive. Again, while the studies of greater cross-country syndication didn’t extend into Canada, it is easy to extend this trend cross-border. A drive could be to focus on those sectors requiring specialized skills such as medical technologies and life sciences.
  • There were a lot of great sessions on emerging, and ongoing, issues, such as crowdfunding, the new SEC Regulation A+ (mandated by the JOBS Act to simplify raises up to $20 million even from non-accredited investors), an ever increasing push to build new and innovative Angel Funds and even post investment Board governance.
  • In that vein, I ran an open panel on “Best Practices to Build a Private Equity Portfolio – Tools and Strategies”.  What was notable was how primitive such angel portfolio management really was. One participant suggested angels portfolio management was comparable to that of public company portfolios 100 years ago. As Angels learn that a passive approach with little portfolio management is sub-optimal, leading Superangels, the advanced Angel groups and the trend to angel funds are all pushing for more professional portfolio management. Although historically they have worked separately, the increased involvement of Family Offices in the world of angels is also starting to drive greater portfolio discipline. New software tools are emerging to help here as well, such as Seraf – Portfolio Management for Angel Investors which was built by angels unable to find a way to automate their portfolio management.

In summary, ACA Summit 2015 was a fabulous opportunity to meet, network and learn from some of the best global angels and understand about emerging models and best practices. Many side bar conversations, dinners and drinks in the garden were packed with wisdom from around the world.

In October, our own NACO Summit will be a great opportunity for Canadians to similarly share and learn and to connect with a more global perspective as our Angel ecosystem continues to grow from strength to strength.

2015 National Angel Capital Summit

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The acquisition of MKS by PTC in 2011, caused me to reflect a bit on what good acquisitions might look like and what they might teach us about building (sometimes elusive) long term shareholder value. As a result, over the last 6 months, I’ve progressively assembled a collection on the most significant acquisitions in the Waterloo area. To my knowledge, such information has hitherto never been collected. We all love to speculate, but it is more productive to ground that speculation with facts.

The following table is intended to summarize value creation through the lens of several key benchmarks. Read the full article →


Typical Modern Meeting - Face-to-face or virtual?

“Expectation is the mother of all frustration.” – Antonio Banderas

Meeting requests are an amazing invention. Pioneered, and standardized, almost 20 years ago by companies like Microsoft (as part of Outlook/Exchange), Novell (Groupwise) and Lotus (now part of IBM Lotus Notes) this innovation had great promise to automate an essential, yet completely routine, aspect of modern life.

The ascendency of meeting request usage, also rides several trends:

  • In the 1990s, I had an Executive Assistant who scheduled my time, acted as a “gatekeeper” and also worked on many projects. She was a master tactician who managed to keep 3 or more Type A executives productively multi-tasking. In many ways, sadly, such personal assistance is being subsumed by..
  • Increasing computational power means that automation of routine tasks, personalized to the needs of individuals is much more of a reality,
  • The mobile revolution has made meetings much more multi-modal and virtual, but also means that most executives must be productive even while being mobile nomads, and
  • Calendars have migrated from paper – I switched about 20 years ago – to desktop computers using Outlook and the like, and now to the ubiquitous smartphone and tablet devices. Such mobile devices are both convenient for calendars, but also frustratingly fiddly places to enter complex meeting details.

Thus, enter the humble Meeting Request which has swelled in popularity. I received my first such request from an Outlook/Exchange user around 2000 and they remained rare until perhaps the last 5-10 years. Now they seem to be everywhere.

In homage to my friend and colleague, Jim Estill, the quintessential time management guru, I ought to be cheering this time saving invention.

And, yet my enthusiasm is sorely tinged by a frustrating implementation resulting in suboptimal user experience …

Top 10 Meeting Request FAILs:

  1. Trojan Horse: It has always seemed odd to me that a thiFrustrating Meeting Requestrd party inviting me to a meeting could embed their own meeting information in my calendar, and yet I am unable to edit this “foreign” request that has invaded my calendar.
  2. Split Personality: If Jennifer invites me, Randall,  to a meeting, then why does my meeting title say “Meeting with Randall” instead of “Meeting with Jennifer”? Computers are designed to automate routine tasks so there is absolutely no excuse for this one.
  3. No Annotation: I write comments in the notes fields of my calendar all the time. Why can’t I say, for example, “Joe is a bit dodgy” or “First met back in 2001”?
  4. Duplication: Many times I receive a meeting request for a meeting that I have already carefully crafted an entry in my own calendar. Again, computers are supposed to be smart enough to figure these things out and merge them in an intelligent way.
  5. Bad Versioning: Many times when meeting information is changed, such as time or venue, the update isn’t seamless. For example, it is common to have both the original and the updated version lingering in my calendar.
  6. No Scheduling: Meeting requests are often used as trial balloons in trying to schedule busy people into meetings. The endless rounds of “Accept”, “Maybe” or “Decline” responses can end up being quite frustrating, especially for many person meetings. These, often fruitless, interchanges underscore the fact that meeting requests don’t automate routine scheduling. Instead, people have to resort to tools like Doodle to vote on alternatives, and then manually schedule the winning result.
  7. Verbosity by having superfluous words in the limited real estate of the meeting subject line. E.g. pre-pending “Invitation:” or “Updated Invitation:” onto the front of a subject, effectively burying the important words. Many times they are put there to increase the impact and readability of the email subject line to ensure opening, but distract in the actual Calendar entry.
  8. Invitations from Google Enterprise Apps or GMail tend to be the most arcane and ugly. Originally, I chalked this up to Google Calendar‘s relative immaturity compared to Outlook, but the brutally long notes and long subject lines continue to stand out as worst in class, almost to the point that I dread getting invited by Google users.
  9. Lack of Anticipatory Computing: in an age where mobile devices know location, existing meetings and other personal habits, the trend to predictive intelligence could be incorporated into smarter meeting requests. For example, combining meeting requests with shared “Free/Busy” data could remove many manual scheduling steps.
  10. No Personalization: Like my contact list, I put a fair bit of thought into crafting a calendar that is both useful now, but also provides a detailed audit trail of my business interactions. To do this, I use conventions, categories and other techniques that, sadly, cannot be injected into these un-editable meeting requests that instead reflect the third party initiator’s preferences.

Do let me know in comments if I missed any major points.

Given the power of networked computing to automate, why is there such a lack of excellence and progress in this particular area?

In fairness, I believe that part of the problem lies in the interplay between competition and the vagaries of formal industry standards. That said, this should be no excuse.

It is admirable that, unlike word processing formats, the various pioneers started to develop standards call iCalendar (and later vCalendar) around 1997 to standardize file formats (like .ical and .ics) and email server interactions. I do know the Microsoft attempted to extend the functionality with some very useful things around that time. But, for some reason, a great idea got off to a good start, but seems frozen at an almost Beta level of functionality.

To conclude, please read this post, not as a gripe, but instead as a call to action to developers to help take the humble meeting request to the next level of user experience. Any takers?



Fall Of The Wall – 25 Years Later

November 9, 2014

A mere 25 years ago, the Fall of the Berlin Wall rent the “Iron Curtain” asunder, a re-ordering of western civilization possibly unparallelled since the fall of the Roman Empire.

25 years and 15 days ago, almost by happenstance, I drove the Berlin Corridor, travelled via Freidrichstraße Station behind the Berlin Wall and witnessed an exhausted and bankrupt regime about to collapse.

Today the

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Business Strategy

Canadian Angel of the Year Award

October 3, 2014

At the NACO Summit in Québec City, it was truly humbling to receive the Canadian Angel of the Year Award. I see this partly as a calling to be an ambassador to continue to help raise the Angel bar in Canada in the coming years. I wish to thank all those kind colleagues who, unbeknownst to me, wrote letters of nomination. Also,

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The Group of Seven – Nation Building for the 21st Century

January 14, 2014

Last year, I signed up for a wonderfully ambitious initiative spearheaded by our Governor General, His Excellency David Johnston. I was invited to join a Group of Seven who will serve as catalysts to rolling out David Johnson’s vision of a Smart and Caring Nation built by a set of Smart and Caring Communities, ultimately aimed to be a major

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Ice Storms Highlight Canada’s Obsolete Infrastructure

January 1, 2014

As we enter 2014, well into the 21st Century, one lesson for me from the year just past was that Canada seems to be hobbled with 19th century infrastructure. Let me explain.

During 2013, my home in Ontario was subject to not one, but two, different ice storms – in April and December. Both brought down large chunks of trees and

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Business Strategy

“How ya gonna keep ‘em away from harm?” – The Sequel

November 22, 2012

Almost four and a half years ago, I penned what some called the obituary of Blackberry (see “How You Gonna Keep ‘Em Down on the Farm”). My intentions in writing that missive were, in fact, quite the opposite.  Back in 2008, a year after the first iPhone, Blackberry didn’t appear to be heeding the threat of major market disruption, let

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Business Strategy

Tech Terroir

October 29, 2012

In the world of wine, the concept of terroir describes a centuries long process in which the climate, soil, grape varieties and dedicated vintners, symbiotically develop a unique “sense of place” for a wine region. A favourite of mine, the garrulous  and quintessential Californian vintner, Randall Grahm, while trying to establish the old World notion of terroir in California postulates that it

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