Some advice for Mr. Wonderful

Kevin O'Leary has officially joined the race for leader of the Conservative Party of Canada. (c) 2017 Kevin O'Leary campaign

Colourful TV personality and successful businessman,
Here are three(ish) entirely unsolicited pieces of advice for Mr. O’Leary:

  1. Talk about growing the economy. That’s your strength. You’re well-informed about the markets and business – and people find you credible on these issues. Talk about growing GDP as the panacea only you can deliver.
  • Don’t talk about anything else. You’re not particularly well-informed on other federal issues such as defence and foreign policy – yet. There be dragons. The opinions you’ve already expressed on these matters are based on myths that belie your unfamiliarity with the details. They’re also anathema to most current Conservatives whose support you will want on the 2nd & 3rd ballots.


  1. Build a new Conservative Party. Focus your efforts on attracting new, younger members into the Conservative Party with a promise to re-shape the Party in their likeness. Maximize your public presence and existing following to convert your Canadian fans into Party members. Then, get them to show up and vote for you. Patrick Brown sold 80,000 memberships in a Party that had only 9,000 members to start with.  Build the O’Leary Party. You don’t have a big team – or much support at the working organizer level in the party, so you’ll have to take a radically new approach that leverages your strengths in mainstream and social media.
  • Don’t ignore existing Party Members. You can’t count on a lot of support from traditional Old Blue Conservatives, but they can still help you win. It’s a ranked ballot system where members pick their 1st, 2nd, 3rd choices, etc. Acknowledge that many of them have already pledged their support to other candidates with whom they have long-standing relationships. Ask for their second choice – or third. Aim to be in the top 2 on that majority of ballots cast. A big field will split the first ballot broadly. The 2nd and 3rd ballot choices will choose the winner.


  1. Suck up the Oxygen. Continue to own the spotlight and use it to set the debate agenda. Drive media coverage of the leadership race in your direction – to your issues and your strengths. Keep your message positive and focused on the economy. Focus on Trudeau as your enemy – economics and the budget are his Kryptonite. Continue to not attack fellow Conservative candidates – in fact, ignore them. You don’t want to offend their supporters whose 2nd ballot choices you want, and you don’t want to dilute the spotlight. Talk like the leader. Act like a winner. Existing Party members want to back a winner.
  • Don’t believe your own press.  Truth is, you do have a money problem because you can’t spend yours.  So, you need to seek donations. The spending limit is $5 million and you should expect to spend all of that – plus whatever it costs to raise it.  French actually is important – though not crucial. You can win without it, but it will severely limit your options and freedom of movement. Keep learning. You can’t do it all with New Members – They often don’t vote. So, even if you sign them up, they may not show up to support you.  And, even if they do, they don’t know how to run a Party so you’ll have to get along with caucus and the Old ‘n Bold at some point.


Is that all it takes?

No. But, it’s a start. There’s a lot more. But, from what I’ve seen, Kevin O’Leary is a pretty quick study.

Can O’Leary win?  

Yes. So could Rob Ford, Patrick Brown and Donald Trump. But, like each of those men, O’Leary will have to find his own, unique path to victory. Will he win? Only time will tell.