Interviews
Legacy and selling a business, and the long game of integrity.
What if selling your business wasn’t just about getting the highest price but about protecting your legacy, your values, and everything you’ve built?
In this powerful episode of Unapologetic Leadership, Cory Dunham sits down with Karl Sigerist, a mergers and acquisitions advisor who has helped generate over $4 billion in transactions, to reveal what most business owners get completely wrong when it comes to exiting their company.
The reality is eye-opening up to 80% of business sales fail, often because owners aren’t prepared emotionally, strategically, or financially. Karl breaks down why having a clear “why sell” is just as important as knowing your numbers, and how a lack of clarity can cause deals to fall apart at the last minute. This conversation goes far beyond tactics. It dives into identity, purpose, and what happens when you separate yourself from the business you’ve spent decades building.
You’ll learn how to properly value your business, avoid costly mistakes, and think like a sophisticated seller even if you’ve never gone through the process before. Karl also shares why integrity isn’t just a personal value. It’s a long-term strategy that compounds over time, building trust, opening doors, and ultimately increasing the value of your company.
What owners get wrong and how to get it right.
In our conversation, we explore:
- Share sale vs. asset sale — and why it matters more than most owners realize
- How to properly use the Lifetime Capital Gains Exemption (and how many miss it)
- Why serious preparation should begin two to five years before a sale
- The most common mistakes entrepreneurs make — especially owner dependency
- Why clean financials, GAAP discipline and a quality of earnings report matter
- Customer and supplier concentration risks in today's geopolitical environment
- What buyers actually look for — and why "value" is always buyer-specific
- The current state of the Canadian M&A market — especially for mid-market and sub-$3-million EBITDA companies
It's about real exits, real retirement outcomes and helping founders understand the difference between what they think their business is worth — and what the market will actually pay.
Know your why.
It was a pleasure joining Elizabeth Shea on the Branching Out podcast to discuss the thinking behind my new book, Selling Your Canadian Business.
We talked about the importance of asking yourself why you're selling, hiring a team of experts, engaging with multiple suitors and knowing that the sale of your business requires much more strategy and preparation than selling a house.
My goal is to help Canadian founders and families ask the right questions and set themselves up for a successful sale before pressure sets in.
Key quote about the importance of defining your "why" to prevent yourself from getting cold feet at the last minute: "One of the first reasons that transactions don't close is the seller has cold feet."
From Angel to Exit.
Karl shares insider strategies on how founders can prepare for a high-value exit. With decades of experience on both the buy and sell sides, Karl reveals why 80 per cent of lower middle-market deals fail — and how you can avoid becoming a statistic. Learn the must-have foundations for exit readiness, how to think like a buyer and why building a culture of preparation pays dividends. A must-listen for founders scaling toward a sale or acquisition.
Key takeaways:
- 80 per cent of lower middle-market exits fail due to poor preparation and unrealistic valuations.
- Clean, audited financials are essential for attracting serious buyers.
- Valuation is driven by future cash flow, quality of earnings and industry comparables.
- Strategic buyers and micro PE funds require different approaches — know your audience.
- Scaling past $1-million to $3-million in EBITDA significantly boosts your exit multiple.
- Succession planning is non-negotiable; your business must be transferable.
- Founders should think like buyers — objectivity creates better deal outcomes.
- Exit planning should begin five to 10 years in advance, not six months before a sale.
Is your business an acquisition target.
Take the quiz to find out, be sure to grab Karl’s book: Selling Your Canadian Business.
Why 80% of Canadian business owners may never sell.
We’re discussing the complexities of selling your privately held business, an important yet often challenging process, especially for owners nearing retirement. As many business owners consider transitioning out of their companies, understanding how to make your business an attractive acquisition target and navigating proprietary deals becomes vital.
Why $5-million to $50-million companies are underserved in traditional M&A processes
Talking to Colleen O'Connell-Campbell of RBC Dominion Securities.
Here is what we talked about:
- The importance of long-term planning and education before an exit
- Why you should start exit preparation 2-3 years in advance - or earlier
- How cultural fit between buyer and seller drives long-term success
- How private equity can protect rather than destroy value
- The difference between a transaction and a journey
- Why you shouldn’t fall in love with your business - and how to prepare it for its next owner
Is "now" the time? What older owner-operators are thinking, post-pandemic.
Mario Nigro’s guest for this podcast is Karl Sigerist, a business advisor focusing on the lower midmarket. Many of Karl’s clients are owner-operators who are thinking about exits. He and Mario discuss the value of engaging an outside advisor and, in particular, the impact that the pandemic has had on the succession strategies of many long-time operators who recognize that new energy may be needed, sooner rather than later, to drive their businesses forward in a changing world.
Search Fund Investor Forum
Ep. 40 | Karl-Sigerist ICD.D BoardMember; Angel One/Equation Angels
