For most investors, “private markets” has always meant one of two things: you’re either in the club, or you’re not.

If you’re a PE fund, a family office, or you grew up in the right nepotism circles, you get a steady stream of small business deals crossing your desk.

If you’re not in that world, you get the leftovers. Otherwise, you’re limited to public markets, or if you’re lucky, the occasional friend’s startup. Even if you’re an accredited investor with $1M+ in investable assets, you’ve historically had no clean path to participate in the exact kind of deals that quietly build generational wealth: boring, profitable businesses changing hands.

That access problem is colliding with a much bigger wave that’s already in motion.

Canada is in the middle of a business succession event that the traditional M&A ecosystem can’t absorb. Thousands of boomer-owned SMEs in the $5 to $30M enterprise value range need to transition in the coming years. Not “should,” but are literally running into the final seconds of the game clock. Owners want to retire, partners want liquidity, and the next generation often doesn’t want the keys. The result is more deal flow than the usual buyers (PE firms, strategics, searchers) can realistically handle at once.

Many of the best opportunities will never go live on the marketplace. They’re private-market transactions. Management buyouts. Deals where a PE firm cold-approaches a business owner and invests directly into the company.

At Breakwater this year, we’ve seen more of these opportunities than in the last seven years combined. CEOs looking for capital partners to close the “equity gap” between bank and seller financing. Operators raising an SPV to acquire an equally sized competitor. Owners who want to stay on post-sale and partner with someone on the next chapter. What makes these deals interesting is that the primary operator stays put, which dramatically reduces the usual owner-dependency risk.

I was talking to a buyer the other day who bought a small business a couple years ago. He was walking me through the cash-on-cash math on the deal and the number came out to over 100% annually. That’s before counting any growth in the equity value of the business itself.

The kicker: his total cheque into the deal was less than $100,000. He’s since gone on to acquire 3 more companies.

These are the kinds of opportunities that occasionally cross our desk at Breakwater, and until now, we haven’t had a clean way to share them. They go to the same 10 people, quietly, and everyone else reads about the returns five years later in a LinkedIn post.

Which is why we’re pleased to announce The Trading Post.

Our free email distribution list for private investment opportunities in Canadian small businesses.

If you want in, apply HERE*

*Must meet accredited or permitted client standards to join.

idea of the week 💡

Credit: ideabrowser.com

  • Problem: Most accredited investors don’t have a consistent way to evaluate private deals. They see a PDF, a teaser, maybe a data room link, and then try to reverse-engineer whether the price, the structure, and the operator actually make sense. There’s no standard underwriting layer for the long tail of SME deals.

  • Idea: Underwrite is a private deal underwriting copilot. Upload a teaser or CIM, and it generates a first-pass underwrite: normalized financials, red flags on add-backs, comparable transaction multiples, and a structure recommendation (equity vs. convertible vs. seller note). Built for angel investors, family offices, and small funds who review 50+ opportunities a year but can only do proper diligence on a handful.

  • How it makes money: $199/month for individual investors, $999/month for small funds and family offices with multi-seat access. Upsell into a marketplace where vetted deals from partner brokerages and EMDs get surfaced to investors who match the profile. The tool is the wedge. The deal flow is the moat.

  • Why it might fail: Investors don’t want another dashboard. They want a second opinion they trust. Start with 20 active angel investors, ship weekly based on their real deal reviews, and measure whether they actually close more deals per quarter. Trust is earned one underwrite at a time.

workouts this week

at-home

EMOM for 20 minutes:

  • Minute 1: 15 burpees

  • Minute 2: 20 air squats

  • Minute 3: 12 push-ups + 30-second plank

  • Minute 4: 20 mountain climbers + 10 jump lunges

Repeat for 5 rounds. Whatever time is left in each minute is rest.

gym

Full body strength day. 4 sets of:

  • Front squat: 6 reps (heavy) + Box jumps: 6 reps (superset)

  • Weighted pull-ups: 6 reps + Dumbbell bench press: 10 reps (superset)

  • Romanian deadlift: 8 reps + Walking lunges: 12 each leg (superset)

  • Farmer’s carry: 40m + Hanging leg raises: 12 reps (superset)

Tips:

  • Rest 90 seconds between supersets

  • Stay heavy on the compounds, controlled on accessories

outdoors

  • 1km jog (warm-up)

  • 5 rounds: 300m run, 15 push-ups, 20 jump squats, 10 broad jumps

  • 1km jog (cool-down)

  • Finish with 3 minutes of stretching

tweet of the week

Super interesting SBA data put together by Justin. If you are curious about acquiring small businesses, make sure to bookmark this page.

my plugs

every second counts

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