Life After Exit: What Comes Next

Selling your company is a major life transition. Here's what I wish I knew before my first exit.

The Emotional Rollercoaster

Immediate Post-Exit

• Relief and excitement
• Sense of accomplishment
• Financial security
• Freedom and possibility

3-6 Months Later

• Loss of identity
• Missing the team
• Lack of purpose
• "Now what?" feeling

This is normal. You've just ended a major chapter. Give yourself time to process.

Financial Planning

Immediate Actions

1. Don't Make Big Decisions Wait 6-12 months before:

• Buying expensive toys
• Making large investments
• Starting new ventures
• Moving locations

2. Assemble Your Team

• Wealth manager
• Tax accountant
• Estate planning attorney
• Insurance advisor

3. Tax Planning

• Understand tax implications
• Consider timing of payments
• Explore tax-efficient strategies
• Plan for earnout taxes

4. Diversification Don't keep everything in one asset class:

• Real estate
• Index funds
• Bonds
• Alternative investments
• Keep some cash

Long-Term Strategy

Wealth Preservation

• Focus on not losing money
• Diversify across asset classes
• Avoid get-rich-quick schemes
• Work with fiduciaries

Estate Planning

• Update will and trusts
• Consider charitable giving
• Plan for estate taxes
• Protect assets

Insurance

• Umbrella liability policy
• Life insurance review
• Disability insurance
• Long-term care insurance

Finding Your Next Chapter

Common Paths

1. Start Another Company Pros:

• You know how to do it
• Access to capital
• Network and credibility
• Passion for building

Cons:

• High stress
• Time commitment
• Risk of failure
• Hard to replicate success

2. Angel Investing Pros:

• Help other founders
• Stay in the game
• Potential returns
• Flexible time commitment

Cons:

• Most investments fail
• Requires expertise
• Can be time-consuming
• Emotional attachment

3. Advisory/Consulting Pros:

• Share your expertise
• Flexible schedule
• Good income
• Low risk

Cons:

• Can feel like work
• Client demands
• Less impact than operating
• May not be fulfilling

4. Take Time Off Pros:

• Recharge batteries
• Spend time with family
• Travel and explore
• Figure out what's next

Cons:

• Can feel aimless
• Hard to restart
• Social pressure
• Identity crisis

My Recommendations

Year 1: Decompress

• Fulfill earnout obligations
• Take a real vacation
• Spend time with family
• Explore interests
• Don't commit to anything big

Year 2: Explore

• Try different activities
• Angel invest (small amounts)
• Advise startups
• Learn new skills
• Meet interesting people

Year 3+: Commit

• Choose your path
• Go all-in on something
• Build new identity
• Create new goals

Common Mistakes

Rushing Into Next Thing Take time to figure out what you really want. Don't start a company just because you don't know what else to do.

Lifestyle Inflation Just because you can afford it doesn't mean you should buy it. Maintain reasonable lifestyle.

Losing Your Network Stay connected to your industry and community. Relationships matter more than money.

Ignoring Health Use your freedom to prioritize health:

• Regular exercise
• Good sleep
• Healthy eating
• Mental health

Not Giving Back You've been fortunate. Find ways to help others:

• Mentor founders
• Support causes you care about
• Share your knowledge
• Create opportunities for others

Finding Meaning

Questions to Ask Yourself:

• What problems do I want to solve?
• What brings me energy?
• What legacy do I want to leave?
• How do I want to spend my time?
• What would I do if money wasn't a factor?

Warning Signs:

• Constant boredom
• Feeling unfulfilled
• Missing the grind
• Envying others' success
• Regretting the sale

If you're experiencing these, it's time to find your next challenge.

The Reality

Selling your company doesn't solve all your problems. It creates new ones. But they're better problems to have.

The key is being intentional about your next chapter. Don't let it just happen to you. Design the life you want.

After four exits, I've learned that the journey matters more than the destination. Find something you're passionate about and go build it. The money is just a tool to enable the work that matters to you.