In partnership with

Welcome back fellow investopreneurs!

In this week’s episode, I’m joined by Jonathan Jacobs, founder of Digital Natives Group, to break down how he built a bootstrapped digital agency from zero into a 7-figure business that ultimately exited to Accelerate360.

We unpack the hard-earned lessons from a decade in the trenches: why starting without an exit in mind quietly limits your options, how having too many partners can box you into bad decisions, and how Jonathan built a 90%+ referral-driven business through relationships.

If you’re building a service business, thinking about an eventual exit, or wondering what really happens after the deal closes (including integration failures, culture clashes, and why most acquisitions struggle)…. this is a conversation you’ll want to pay close attention to.

The Seven Hard Truths About Building an Exit-Ready Business

(That Most Founders Learn Too Late)

Most founders don’t plan for an exit…
They end up in one.

A buyer shows up…
A partner wants out…
Burnout hits…
Life forces a decision.

That’s when they realize the business they built… while successful on paper… has quietly removed most of their options.

Bad cap table decisions…
Too many partners…
No systems without them…
Revenue that looks good but isn’t transferable.

Exit-readiness isn’t something you “add later”…
It’s something you build into the business early, when you still have leverage.

After hundreds of conversations with owners who’ve sold, tried to sell, or wished they could, these seven truths show up again and again.

They aren’t theory…
They’re pattern recognition.

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#1. Define Your Finish Line Earlier Than Feels Comfortable

Most founders can tell you their revenue goals.

Very few can tell you…

• How long they want to run the business

• What role they want to play long-term

• Whether they want liquidity, control, legacy, or freedom

Those answers matter before you scale.

A business built for…

• A strategic sale

  looks very different than one built for…

• A PE recap

  or…

• A family-owned asset

  or…

• A lifestyle business

If you don’t define the destination early, every decision becomes reactive…

• You take capital because it’s offered

• You add partners because you’re overwhelmed

• You scale because it feels expected

Five years later, you’re “successful”… and stuck.

Define what success actually looks like before the structure hardens.

#2. Too Many Owners Kill Optionality

Early-stage equity feels cheap…
Later, it becomes the most expensive thing you gave away.

Multiple equal partners create three problems…

1. Slower decisions

2. Misaligned incentives

3. More people who need liquidity

Four equal partners means…

• Four timelines

• Four risk tolerances

• Four definitions of “enough”

Buyers hate complex cap tables…
They discount value when deals can be blocked or slowed by internal dynamics.

Equity should solve long-term alignment… not short-term capacity problems.

If you already have too many partners, start addressing it now…
If you don’t… be extremely cautious about adding them.

#3. Relationships Are a Stronger Moat Than Margins

The most valuable businesses don’t rely on ads…

They rely on relationships.

A business that grows primarily through referrals…

• Has lower acquisition risk

• Has higher trust

• Is more resilient during transitions

• Is more attractive to buyers

But referrals don’t happen by accident…

They come from…

• Showing up consistently

• Being part of real communities

• Investing in relationships that don’t pay immediately

Many founders stop doing this work once revenue grows…
That’s a mistake.

The pipeline you have today is often the result of work you did years ago.

Relationships compound…
Neglect compounds too.

#4. You Can Only Win Two of These Three

You cannot sustainably optimize for all three…

• Great work

• Great relationships

• On-time delivery

Something always gives.

The best operators choose their trade-off intentionally…

• Some prioritize quality + relationships

• Some prioritize speed + reliability

• Some prioritize expertise + execution

Problems start when founders pretend they can do all three… and burn out trying.

Pick your two…
Design the business around them…
Communicate it clearly to clients and your team.

#5. Systems Matter More Than Talent

Buyers don’t buy effort…
They buy predictability.

If the business only works because you are there…

• It’s fragile

• It’s risky

• It’s discounted

Exit-ready businesses have…

• Documented processes

• Repeatable delivery

• Teams that function without constant founder intervention

This isn’t about bureaucracy…
It’s about transferability.

If someone else can’t step in and run it, you don’t own a business… you own a job.

#6. Integration Is Where Most Value Is Lost

The deal closing isn’t the finish line…
It’s the starting line.

Most failed exits don’t fail on price…
They fail on integration.

Culture clashes…
Team turnover…
Broken handoffs…
Earn-outs that turn adversarial.

Smart buyers plan integration early…
Smart sellers do too.

If you ever plan to exit…

• Document how things actually work

• Reduce tribal knowledge

• Understand what makes your culture effective

• Prepare your team for change

A great deal can be destroyed by poor execution after close.

#7. Know Your Personal “Enough”

This is the hardest one.

If you don’t define “enough” for yourself, you’ll always chase more…

• More revenue

• Higher multiples

• Bigger exits

And still feel dissatisfied.

Your “enough” isn’t just money…
It includes…

• Time

• Stress

• Identity

• Control

• Health

• Family

Some founders exit for eight figures and feel lost…
Others grind for years past what they actually needed.

There’s no right number…
But there is a wrong time to figure it out… during negotiations.

Know what you’re building for…
Build equity to serve your life, not replace it.

Final Thought

Exit-readiness isn’t a checklist you complete at the end…

It’s a posture you adopt early…

• Fewer constraints

• More optionality

• Better decisions over time

The founders who win aren’t the ones who hustle hardest…

They’re the ones who…

• Structure intentionally

• Preserve flexibility

• Build businesses that can survive without them

Start earlier than feels necessary.

Your future self will thank you.