Making a Big Dent - Boomer Entrepreneurs

A Friend of mine recently approached me at a social with a huge smile on his face - it was the happiest that I had seen him in months. He was so excited it was hard for him to blurt out the words: "I am free - I resigned my big corporate job last week and plan on starting my own gig - I am charged up and can hardly wait to shift gears and get my venture out of the gates."


Being the "Entrepreneur's Entrepreneur" that I am, I got caught up in the passion of the moment. "Congratulations my friend you are now joining the unique and growing club of "Boomerpreneurs" - there will be no looking back from this point on."


As best as I can tell, the phrase "Boomerpreneur" was coined a couple years back and written about extensively in the National Post (Chevreau), Business Week, Wall Street Journal and USA Today to name a few. I even found a dedicated Blog on the subject.


A Boomerpreneur is a individual born between 1947 and 1966 who has started their own business. In Canada, this age group represents about a third of the total population and is estimated to control about 65% of the wealth in the country. A study done by Delta Economics (Dec 2008) suggested that over 30% of the Entreprenuers in the US were over 50 years of age. A formidable force indeed!

I have a significant portion of my clients who would be classified as Boomerpreneurs. I am always interested in how they got to formulating their business ventures. Here are a couple of quotes:

• "I needed to get off the Trend Mill and have some Fun. I been functionally trained by my corporation in all aspects of business - its time to put those skills together for me."


• " The Recession has kicked the stuffing out of my retirement nest egg. I need to go back to work to supplement by retirement annuity."


• "I met a couple of young guys with some ground breaking technology. They need some leadership and grey hair on their team to make this a reality. Joining up with them is forcing me to dig deep and remember some those skills that have not been exercised in a while."


• "My daughter recently started her own business. I was looking for something to keep me occupied. What better way to rejuvenate my working career - with your family."


• "I have always dreamed about owning my own business. I was lucky in that I could turn one of my hobbies into cash flow - I am having the time of my life."


• "Take, Take, Take - it's time for me to Give Something Back."

Thinking of becoming a Boomerpreneur? - Here are a couple of things to think about:

1) Personal Inventory- Not everyone will be cut out to be a Boomerpreneur. Create a series of lists - What you like to do? What you hate doing? What are your core skills? What are you lacking? What puts a smile on your face? What would you like to do before your number is up? These lists will give you an honest assessment of who you are and what you could be passionate about.

2) "The Thing" - For some "The Thing" is something that they have always wanted to do perhaps a hobby that could develop into a business. For others it may be joining forces with another Entrepreneur who already have the idea and needs a partner.

3) Networking - Help for your idea will come from many sources including family & friends and other early stage Entrepreneurs trying to get there business off the ground. Input from all sources will enhance the shaping of your thinking.

4)Build a Plan - You can't just jump into this without a "plan of action". This plan may start out on the infamous "cocktail napkin", progress to a "two pager", a powerpoint and then finally a 25 page business plan. Regardless of its form, you will need research, assumptions, validations, financial models, Go to Market implementation plans as well as risks and contingencies.

5) Brand - I am a big believer in creating your Brand (vision, mission, logo, website) and getting your messages out there. You will probably need some professional help in this regard.

6) Understand the Implications - Becoming your own boss has a significant set of implications on your time, quality of life, family, cash flow and personal being. Create a list of implications and associated stakeholders. Be sure to constantly review your progress and its associated impact. Be prepared to "course correct" a number of times.

7) Assess and Celebrate - Constantly review your progress to your "plan of record". Celebrate the wins regardless of the size and revisit the reasons that things did not go according to "Hoyle".


For those who have made the leap, I can truly say that they are in a better place then they were before. I plan on writing a lot more about this phenomena as my friends and clients gain traction as Canadian Boomerprenurs.

Management & Its Ability to Execute

We have seen some exciting new technologies in the past couple of months and our work to "accelerate the path to commercial success" has been intensifying. Of particular interest are some of my clients with Waste to Energy, Solar, Water Treatment and Smart Grid technologies. Those organizations will be the backbone of the Ontario economy in the not to distant future.

As we work work with these early stage organizations, a set of patterns are starting to emerge that are worthy of emphasis. Clearly, these technology companies are focusing in Exciting and Growing sectors. They are based in Science and are well on their way to securing Intellectual Property (IP) protection for their inventions. Businesss models although initially "a little crude", are being re-worked to demonstrate the ability to successfully "turn a profit". Any investor who takes a "quick look" is quickly impressed on all three fronts.

So why aren't we reading more about the successful financing of these companies by Angels, VC's, Government Grants and larger Institutions?


A quick canvas of any investor group will tell you that Management and its Ability to Execute often eclipses the process for securing early stage funding. Due Diligence teams will ask the Leadership team questions such as:

• How many years of experience does the team bring to the table?
• Have you successfully built other organizations to a successful exit?
• Does the CEO have the depth and breadth to move the organization to its next level?
• Are all key functional disciplines appropriately represented by the organization?
• Does the management actually act and respond as an effective team?
• Is the team able to articulate an action plan and deliver those promised results?
• What kind of dashboards are used to track weekly, monthly and quarterly success?

These are extracts of a long list of diligence questions that any investor will need to be comfortable with before opening the cheque book. How about the one that Kevin O'Leary made famous on Dragon's Den: “What if you get hit by a bus and you're road pizza?”

The key for these emerging technology companies will be to do a detailed assessment of their team and its story around executing strategy. The assessment will not doubt uncover several holes in the team that will need to be proactively addressed to mitigate investor risk. These may include:

1. Identifying key hires that will be added once funding is secured,
2. Assembling that Advisory Board and ensuring that they are engaged,
3. Hiring part-time Mentors to work with lessor experienced executives,
4. Encouraging the completion supplementary training programs,
5. Joining key sector networking forums and in some cases,
6. Identifying that the existing CEO may need to step aside in favour of a "been there, done it before" leader.

The good news for Entrepreneurs is that if their technology really is a "Game Changer", the "Path to Profitability" is reasonable and the tactics to augment the "Execution Strategy" are sound, many seasoned investors will take a "serious second look" at the company with great result.

Increasing the Odds of Success

A fellow blogger recently pointed me to a study done by a couple of Harvard business professors (Gompers and Lerner) titled “Performance Persistence in Entrepreneurship”. This study looked at the track record of first and second time Entrepreneurs creating a successful enterprise. (Success was defined as taking the start-up entity public.) The results of the study were chilling to say the least.

They found that first time Entrepreneurs only had a 22% chance of success and for the 78% who tried it again the Entrepreneur was only 23 % successful in their next venture. They also noted that to a certain degree “success breeds success” - the successful ones who tried a second venture were 34% likely to succeed.

This Harvard research and a companion study done by CIBC World Markets in 2005 suggested that successful ventures had a number of consistent characteristics that made them over achieve. These traits included: a) High Level of Education (2 of 3 Canadian Entrepreneurs have post secondary education), b) Extensive Use of Advisers (Service Professionals, Board Advisers, Board of Directors), c) Outsourcing Strategies (Companies focused on core competencies and outsourced other non-core functions), d) Technology Enablement (Companies utilized Web presence, CRM software to enhance and support customer interactions) and e) Focus on US and International Markets (Canada is only the starting point).

This is where the Ontario Commercialization Network (OCN) comes into play. Eight of the 13 centres have been funded with an Entrepreneur In Residence (EIR). These individuals are seasoned executives who have build, sold and turned around a number of ventures in their careers. The role is to “accelerate the path to commercialization” for these early stage companies.

EIR’s in the OCN all have a unique and individual style in advising their clients on "creating the organization's traction". Supported by Provincial, Federal and Private funds, EIR's across the province rely on a core set of resources to support their clients. These include 1) Education and Reference material, 2) Extensive network of contacts and practical experience, 3) Market Research, 4) Executive Coaching and Mentoring, 6) Assistance in building a Compelling & Focused story.

Entrepreneurs are the key to Ontario’s innovation agenda and are encouraged to sign up with the Commercialization centre in their region. We need to do all we can to increase their odds of "Stunning Success".

M&M's - Paramount for Success

M&M's are critical to a company's success and I don't mean the plain or peanut kind! Measurement & Management Dashboards are important tools for building sustainable success.

A couple of months agoTerry Matthews - a great Canadian icon was speaking at a MaRS event about his success model for start-up organizations. Having started over 80 successful organizations in the past 25 years, he has a record of credibility. Terry explained that one of the keys was to have each of his organizations' create a monthly report that measured a number of indicators in the Rear View mirror (We Accomplished this, We achieved that, We we unsuccessful with this.) and out of the Front Windshield (We plan on completing this, We are Scheduled to achieve that). These monthly Dashboard reports were prepared by the CEO as if the company were publicly traded on the TSX - a great standard of Governance.

For my clients at the RIC-Centre I am also encouraging the drafting of these telltale M&M Dashboards that cover the important facets of their start-up. The CFO and CEO need to ingrain that culture of measuring and taking management action in their early evolution as an organization. Measurements should cover the basics of financial reporting but also drill down a number of layers on key indicators such as Customer Acquisition, Product Development, Human Resourcing, Regulatory Approval, Channel Development etc. The clarity of the historic indicators and forward looking statements will do wonders for the focus and accomplishment of these early stage organizations.

Many of my Followers are also curious to hear about how the High Handicapper is making out. After a couple more lessons, hours on the practice tee, a loud shirt and 15 rounds later - there is considerable improvement. "Jimmy the Genius" continues to work his magic - the hard work however is clearly in my hands. Following my own entrepreneurial advice I have implemented my own M&M Dashboard process for my journey to a lower handicap.

On the top part of the card I write down the three things that Jimmy has me working on (grip, alignment, aim) for the current week. I also articulate what I hope to Accomplish - 2 less lost balls, gross stroke reduction of 6, 5 less putts for example. This sets the tone and provides a constant reminder of what I am trying to accomplish each time I make an entry onto the card.

In the middle section I create a series of drill down measurements that allow me to manage each part of my trek down the course. Off the tee I note if my ball went where I had intended it to go with a simple check mark. If if doesn't go where it should have, I add additional indicators - did it go Left (L), Right (R)or Duff (D)? For Left and Right I also note if it went Long (LO) or Short (S). For Lost balls I count the number and location -Woods (Wo), Water (Wa) or those nagging ones lost on the Fairway (F). (I decided not to measure Deep Woods or the number of Skips across the pond!) For Putts, I count the Total including the number less than 3 feet and greater than 20 feet. At the end of each hole in addition to my Gross Score I have some interesting statistics to help me M&M at the next tee.

By the way, don't ask me to keep your score as well as mine - There is no room on the card and my M&M Dashboard is all consuming to my focus and Paramount to my Success.

Somtimes you have to go Back to the Drawing Board

One of the greatest things about Entrepreneurs is that they have the persistence to keep trying. We all need to draw inspiration from their spirit.

Having exhausted a host of innovative and creative methodologies to achieve Large Success or Smaller Successes, sometimes the current path will simply not achieve the expected results. If this is the case then it's clearly time go back to the Drawing Board to bring in some fresh thinking and leverage the network of trusted advisers.

In my own personal adventure I am struggling to move my handicap. As a proclaimed Fix-it guy having turned around a number of Technology businesses, I have always viewed that I could fix my game all by myself. I have subscribed to the Books, the Gizmo's, the Over-correction, the Under correction, new clubs, new balls and the golf Channel. I have even listened to my good friend "Lar" who suggested "that's all in way your dress for the game!" I have consistently resisted engaging the Pro as I feared that the re-building would be so disruptive to the pathetic game I currently process. Having struggled through a horrible game on the weekend I came to the conclusion that it's time to go back to the Drawing Board.

We have written in previous blogs about the importance of Trusted Advisers and Board Members as important tools in an Entrepreneur's available network. The same holds true for service providers including legal, tax, accounting & strategic marketing professionals. A couple of my clients are struggling with getting that first customer to say yes. Sometimes it may the simplest of things that will make all the difference so we go through analytic process of deciding what's working, what's not and try to identify who or what will it take to make the customer say yes. Drafting a New Game Plan leveraging on what we know comes out of this process.

For those following the High Handicapper, the Drawing Board indicated that I need to bring in the professional help. I engaged Jim (CPGA guy) to work with me on the range in the pouring rain. (Never really rains on the course). After an hour of work, we identified a simple three things that could consistently straighten out the shots and reduce that score. Applying the advice yesterday was a Miracle! "Jimmy the Genius" has lived up to his reputation. Let's see if I can apply the concepts to a process of continuous improvement.

Just to be safe however I also went out and got that new golf shirt consistent with my colour palette. I wouldn't want to stop receiving that "free advice" from "Lar".

Is Success Spelt with a Large S or Small s?

In our quest to commercialize Ontario's newest Innovative companies, a number of us are struggling with how to measure their progress and the definition of Ultimate Success. Many of my colleagues are big proponents of "the only measure is total number of Jobs Created" others are suggesting that "Revenue, Customers Acquired or Dollars of Investment Attracted" are more applicable indicators of achieving that Home Run.

For my clients, I encourage them to "Think Huge" and try to define their Home Run around their Vision statement. This forces them to become big thinkers and set a Large S target cannot be easily achieved by fixing one thing or completing a couple sub-tasks.

Sharon, an intern at the RIC-Centre did a little research around the Blue Jays this year. She notes that the team has had 3790 At Bats achieving 1020 hits. Of these hits, there have been 649 singles, 240 doubles, 7 triples and 124 Home Runs. The Large S target of hitting that Home Run has only occurred 3% of the times At Bat. Given this low probability, I am sure that the players in the batter box are defining a series of Small s targets like getting to first, not striking out, advancing the runner, not swinging at the the silly sinker etc.

Early stage companies are encouraged to work out a series of Small s targets in all facets of their business. These include completing the necessary business planning, building that unique set of features and services, populating a winning team, securing the first Beta customer, locking in critical financing and driving toward that first quarter of profitability to name a few. Small s successes will be easier to demonstrate short term wins and be an inspirational lift to the Entrepreneural teams. The target of hitting the ball over the Green Monster will come in its own time.

For me Thinking Huge this summer is to drive my handicap under 20. (For many of you this would simply be a Base Hit! You have no idea how big this challenge is for my game.) Now that I have posted this blog, I can head out to the first tee and try to avoid driling it into the woods......

I will celebrate my Small s accomplishments on the patio of the 19th - anyone care to join me?

Those Pesky Independent Directors

A young CEO recently asked for some advice. She had just signed off on a third party investment which came with the requirement to add an Independent Board member to the team. The CEO commented that "The dynamics and complexity of the Boardroom has changed in a number of significant ways. I need some help in understanding what is unfolding." The key changes as she described them included:

1) "The new Independent member has asked for a lot of background material about the company, our shareholders, suppliers, accounts receivable, contracts, payables, risks, issues and opportunities, personnel files, incentive plans - the list was long and the more I provided the more information I was requested to deliver." I respond -it is very important that a new member of the board come up to speed as quickly as possible. Much of the material that you have used in your recent due diligence will provide the Director with the necessary background for an effective Board Orientation.

2) Prior to the meeting, a Detailed Agenda was requested that included a start, stop and time allocation for each agenda item. In addition, we were asked to categorize the agenda into a) Standing Matters (CEO Report, Financial Update, Pipeline Review), b) Committee Reports: (Finance, Human Resources, Governance & Risk) c) New Items: (For Information Only or Decision Required), d) In Camera session (excludes CEO). I respond - this is just common sense. Directors are busy and organized professionals. An appropriate well constituted meeting agenda is critical to ensure meeting efficiency. The Chair of course will need to be strong to ensure that the meeting plan stays on track. An In Camera session without management is a must.

3) A couple days prior to the meeting a detailed Board Package of supporting materials was sent out to all members. Our new board member was looking for at least 5 days with the supporting materials. Twenty four hours in advance of the meeting, the final materials were emailed or faxed - Our new member was happy that the changes to the final package were small. I respond - Directors are appointed to help enhance management's decision making. They will need to see a sufficient level of detail to understand the options and recommendations made by management. Given schedules and commitments 5 days is the minimum period of time to allow the member to read and absorb the materials. Often after the Board Package goes out there are critical updates that need to get sent - these updates should be sent no later then 24 hours in advance of the meeting and should not form the core of the agenda materials.

4) The meeting itself also changed quite dramatically. With all the materials sent out in advance everyone on the Board had a chance to understand where we were at. The board meeting dynamics now changed to a barrage of questions about the assumptions, the trends and associated conclusions related to the materials. I respond - Asking questions helps with the clarity and provides a real time mechanism to test the quality and validity of management recommendations. It is often stated that there are no "wrong questions" in the board meeting. Directors who don't understand a particular point will most certainly speak up.

The Board of Directors are appointed by the Shareholders and their purpose is to "Enhance Executive Decision Making". They are bound by a Duty of Loyalty that demands that they act in the best interests of the Stakeholders. Stakeholders include not only shareholders but customers, suppliers, NGO's, employees, government agencies and others with a "stake" in the companies business. Their Duty of Care is to act in a matter that is consistent with what a reasonable person would do when presented with a similar set of facts.

Directors perform their duties by a) demanding a high calibre Board Package that contains the right amount of detail and is delivered in well in advance of the meeting, b) asking lots of questions to improve clarity and test what if scenarios and c) digging into their wide and deep leadership expertise to help guide management.

The CEO who asked for the assistance left our session with a significantly enlightened view of that Pesky Independent Board member. Does it now make sense to you?