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the $250,000 mistake my client could have avoided

Introducing Exit Navigator, a $650M start-up idea, and 3 workouts to test you this weekend.

Author

Morgan Tate
August 22, 2025

I need to get something off my chest…

I am SICK of watching hardworking entrepreneurs lose money on the sale of their business.

But there is one story that reaaallly frustrates me.

It was a client of mine that sold their business for $1.3M. On paper, it should have been a dream deal. Because of Canada’s Lifetime Capital Gains Exemption (LCGE), the sale would have almost been 100% tax-free.

But it wasn’t.

Why?

  • They had nearly $1M sitting in the corporation as idle cash (making them ineligible for the LCGE).

  • Their CPA didn't flag the issue or do any tax planning (even though they knew their client was going to sell).

  • As a result, they ended up with an unnecessary $250,000+ tax bill.

All because of zero exit planning. Unfortunately, a majority of entrepreneurs leave 25% (or more) of cash on the table when they sell.

This is why I built the Exit Navigator program with Breakwater — guaranteeing a 25% increase in the sale value of your business or we pay you.

Exit Navigator is designed so that entrepreneurs:

  • Avoid costly mistakes that kill deal value

  • Maximize their sale price and walk away with no regrets

  • Prepare in advance so buyers compete for their business, not discount it

Here’s our promise:

👉 If you don’t sell for at least 25% more than your baseline valuation, we’ll refund you $6,000 when you sell.

During the program you also get:

  • Unlimited access to our team (email, phone, text support whenever you need it)

  • Monthly accountability meetings with 30 and 90-day action items

  • ‘Off-Market’ status with access to qualified buyers before you go to the marketplace

  • Discounted fees if you decide to sell with Breakwater (no obligation)

If you (or someone in your network) is planning to sell or retire in the next five years, start with a free business valuation.

Because no founder should regret selling their life’s work.

idea of the week 💡

Credit: Idea Browser

  • problem: Construction firms spend thousands of hours on lien waivers - critical legal documents that gate-keep payments but create massive administrative burden. A single error can freeze payments for weeks.

  • idea: An AI-powered platform that automatically generates the exact waiver needed for each job, state, and payment phase. It integrates with existing payment systems, pulls project data automatically, and creates legally-compliant waivers in seconds.

  • how it makes money: $199-$499 monthly subscription based on project volume, with enterprise plans for larger firms. The market opportunity is $650M+ in efficiency gains from the 100+ million waivers processed annually.

  • why it might succeed: Solves the #1 cash flow bottleneck in construction while providing a strategic wedge into broader construction tech automation. Every waiver processed strengthens competitive advantage.

  • why it might fail: May struggle to reach target mid-sized contractors ($5-50M revenue) who feel the pain most acutely but might be resistant to new technology solutions.

friday fitness

Three workouts for this weekend:

at-home workout:

Complete this endurance circuit 4 times:

  • 20 squat jumps with controlled landing

  • 15 decline push-ups (feet elevated on couch or chair)

  • 30-second hollow body hold

  • 25 mountain climbers with core engagement

Challenge: Rest only 45 seconds between rounds

gym workout:

  • 5x5 deadlifts at 80% of your max

  • 4x8 incline dumbbell press

  • 3x12 cable face pulls for shoulder health

  • Finisher: 100 kettlebell swings broken into as few sets as possible

outdoor workout:

Complete at your local park:

  • 10-minute progressive run (increase pace every 2 minutes)

  • At a bench: 3 rounds of 15 incline push-ups + 20 step-ups per leg

  • Find a hill: 5 hill sprints with walking recovery

  • Final challenge: 3-minute plank meditation focusing on your biggest goal for the coming week

tweet of the week

This one is for all the entrepreneurs selling B2C (thoughts and prayers).

video of the week

I am starting a new content series on the (overly) confusing terminology of M&A - check out one of the first ones below:

my plugs