A New Wave Podcast
From Search to Purchase: Navigating Legal Dos and Don’ts of Entrepreneurship Through Acquisition

Josh Calderon is a legal expert and founder of grit & co law. Josh shares his insights into the legal nuances that entrepreneurs must consider when acquiring a business. He covers practical advice on when to engage legal counsel, understanding the inevitable 'hair' on deals, and how early relationships with legal advisors can significantly benefit business searchers. Whether you're a seasoned entrepreneur or just starting out, this episode is packed with crucial advice for anyone looking to buy a business and navigate the complexities of legal and financial landscapes effectively.
Season 11 — March 17, 2025
5 Key Strategies for Successful Business Acquisition:
- Engage Legal Counsel Early: Connect with specialized Mergers and Acquisitions (M&A) lawyers before you even start searching. This allows them to keep an eye out for opportunities that match your criteria and provide valuable connections to lenders, equity partners, and brokers.
- Accept That No Deal Is Perfect: Every business acquisition has issues or “hair” on it. The key is determining which issues you can live with and which are deal-breakers. Understanding this reality helps set proper expectations from the start.
- Conduct Comprehensive Due Diligence: Use legal counsel to uncover potential liabilities through public record searches and contract reviews. Remember that sellers present favourable views of their business, and your legal team serves as the necessary counterbalance to verify claims about litigation, employee issues, and customer relationships.
- Balance Speed With Caution in Letters of Intent (LOIs): Move quickly enough to remain competitive (within 5 days of receiving a Confidential Information Memorandum), but don’t make offers you intend to walk away from later. Find that 80-90% confidence interval before submitting an LOI.
- Give Proper Attention to Purchase Agreements: Don’t treat purchase agreements as standardized templates. Remember that shorter agreements typically favour sellers, while longer, more detailed agreements protect buyers. This document may be crucial if disputes arise later.
Show Notes:
[00:00:40] Key legal considerations for searchers starting their ETA journey.
[00:01:56] When to engage legal counsel in the deal process.
[00:04:23] How lawyers facilitate deals and connections.
[00:07:53] Why first-time business acquisition is high stakes.
[00:09:42] Why Josh focuses on ETA.
[00:12:25] The role of legal counsel in the due diligence process.
[00:15:45] Asset purchase vs. share purchase in Canada vs. the US.
[00:19:10] Common legal issues uncovered during due diligence.
[00:22:52] The “wild west” of lower middle market businesses.
[00:26:55] Why legal review of Letters of Intent (LOIs) is crucial before signing.
[00:32:24] Balancing competitive offers with due diligence needs.
[00:34:45] Why bully offers typically don’t work for searchers.
[00:36:35] Common pitfalls in share purchase agreement negotiations.
[00:37:33] Why longer agreements favour buyers, shorter favour sellers.
Resources & Further Reading:
Highlights
"There is no perfect deal. I've never seen one in my entire career. There's always gonna be things that a searcher should be aware of. And that's really where the opportunity is because businesses have these issues."
[00:00:54]
"For a searcher, they’re often first-time business buyers and the stakes are so high... And so you may not get a second kick at the can if the first one doesn't go well." [00:07:53]
"The shorter the agreement, the more favourable that's going to be to the seller. The longer the agreement, the more favourable that's going to be to you as the buyer of that business." [00:37:33]
VFC News
29 Trailblazers Join Canada’s First ETA Academy in Toronto
March 21, 2025
2025 Employer Advisory Council: Driving Innovation in Canada’s Startup Ecosystem
February 3, 2025
Pilot Program Creates Startup Opportunities for International Students in Canada
January 17, 2025
Recent
Building Power Skills, Mastering AI Fluency, and Redefining Career Paths for the Future
With Zabeen Hirji

Crafting Sustainable Skincare, Debunking Unicorn Startups, and Fostering Long-term Business Relationships
With Patrice Mousseau

A Cultural Anthropologist’s Take On Intersectionality, Embracing Change, and Venturing Beyond the Norm
With Samantha Stilwell
