Engineering Your Business for a Profitable Exit with JR Rivas

In this powerful interview episode of the Freedom to Exit Podcast, Lani Dickinson welcomes JR Rivas—a young entrepreneur who successfully sold his business by intentionally designing it from the buyer’s perspective. JR dives deep into the realities of preparing a business for acquisition, navigating deal structures, and defining what a meaningful exit really looks like beyond the money.

Start With the End in Mind

JR explains that he and his co-founder made the decision to build their business from day one with the goal of selling it. This meant thinking like a buyer:

• How do we reduce risk?

• What metrics would matter to an investor?

• How can we create recurring revenue, solid customer LTV, and operational independence?

The biggest insight? Preparing for an exit doesn’t just make your business sellable—it makes it stronger.

Create the Deal Room Before You Need It

Lani and JR discuss the concept of a "deal room" (or sandbox): a secure place where your most critical due diligence documents live. JR shares that they began building their deal room a full year before listing the company. That early preparation meant they could:

• Demonstrate team independence

• Show improved financial tracking

• Remove the founder from key delivery roles

Instead of scrambling to build a narrative during due diligence, they had the proof of progress already documented.

Mistakes Made (and Lessons Learned)

Despite their preparation, JR admits they made several missteps:

• Trusting their broker too much without validating fee norms

• Underestimating the complexity of financial reporting (e.g., adjusting entries, compilation reports)

• Signing letters of intent without legal guidance

These lessons taught JR the importance of vetting experts carefully and being crystal clear on what he was and wasn’t willing to accept—especially when it came to broker fees and earn-outs.

The Earn-Out Dilemma

The pair spend a good portion of the episode unpacking the earn-out trap. JR shares a valuable perspective: always assume you might never get the second bite of the apple. He wanted a deal where if no additional dollars came, he would still be satisfied with the upfront cash.

Lani echoes this sentiment with her corporate experience, noting that 73% of founder-CEOs don’t survive through the 5-year holding period in private equity deals—making those promised earn-outs highly uncertain.

Know What You Want Post-Exit

The episode closes with a heartwarming reflection. JR, now 30, doesn’t want more stuff—he wants more life. He’s had the Lamborghinis and the luxury properties, but what excites him most now is the freedom to:

• Travel

• Give generously

• Be present for aging parents

• Eventually start another business—on his terms

His goal isn’t just another startup. It’s creating a life of intentional balance, family connection, and purpose.

Final Thoughts

This episode is a masterclass in what it means to reverse-engineer a business with clarity and intention. JR's story isn’t just about business strategy—it's about personal growth, wise decision-making, and knowing what you’re really playing for.

If you’re thinking of selling in the next few years, you’ll want to soak up every insight from this conversation.

Free Resources to Go Further:

📌 7 Ways AI Can Boost Your Sales and Save You Time - Download this free guide:
👉 https://ai.activatetoascend.com/get-7ways-ai

📌 3 Ways Your Business Can Use AI TODAY to Stop Leaking Money – Save your seat for the free live webinar: 👉 https://webinar.activatetoascend.com/webinar-register-general

📌 Changes Assessment – Discover where your business is leaking time, money, and momentum:
👉 https://stealthfreedomtoexit.com/changes