Nathan Hirsch Profile picture
Aug 30 16 tweets 3 min read Read on X
How to Setup Your Business for an Exit (My Playbook)

I sold my company in 2019.

The process takes time.

Most founders start too late.

They leave millions on the table.

They scramble when buyers show up.

Your exit starts the day you launch.

Here's the exact playbook I used: Image
I. Strategic Foundation (3-5 Years Out)

1/ Define Your Exit Goals

Why? Align all efforts with end goals (e.g., sell to PE, competitor, or employees)

How: "Do I want cash upfront? Legacy preservation? Ongoing involvement?"
2/ Build a Scalable Model

Fix: Shift from owner-dependent to systems-driven (e.g., documented SOPs, autonomous teams)

Metric: ≥80% of operations run without founder input.
3/ Triple Recurring Revenue

Fix: Convert project work to subscriptions (e.g., retainers, SaaS-like contracts)

Target: 70%+ revenue from recurring sources.
II. Financial Optimization (2-3 Years Out)

1/ Audit Financials Rigorously

Fix: Hire a forensic accountant; clean up balance sheets, cap tables, and tax filings.

Must: EBITDA margins >20% (industry-dependent).
2/ Diversify Revenue Streams

Fix: Reduce key client risk—no single client >15% of revenue.

3/ Cut "Add-Backs" Drama

Fix: Document discretionary expenses (e.g., family salaries, luxury travel) as "add-backs" to boost EBITDA.
III. Operational Excellence (1-2 Years Out)

1/ Document Everything

Fix: Create a "Data Room" with:

- SOPs 📁
- Customer contracts 📑
- IP assignments 🔐
- Compliance records 🏷️
2/ Strengthen the Leadership Team

Fix: Hire a seasoned COO/CFO; tie their equity to post-exit retention.

3/ Secure Key Relationships

Fix: Lock in supplier/partner contracts; ensure client agreements are transferable.
IV. Exit Execution (6-12 Months Out)

1/ Engage Advisors Early

Who: M&A attorney, investment banker, tax strategist.

Cost: 5-10% of deal value—but pays for itself in premium valuation.
2/ Run a "Structured Auction"

Process:

- Identify 50+ potential buyers (strategics, PE firms, competitors).
- Share teasers → sign NDAs → solicit bids.

Goal: Create bidding competition.
3/ Prep for Due Diligence

Checklist:

- Financial audits ✅
- Customer churn analysis 📉
- Tech stack documentation 💻
- Employee retention plans 👥
V. Post-Exit Transition

1/ The Golden Handcuffs

Fix: Tie 20-30% of payout to post-close milestones (e.g., 2-year earnout).

2/ Protect Your Legacy

Fix: Negotiate advisory roles, brand usage terms, and non-disparagement clauses.
𝗖𝗿𝗶𝘁𝗶𝗰𝗮𝗹 𝗘𝘅𝗶𝘁 𝗩𝗮𝗹𝘂𝗮𝘁𝗶𝗼𝗻 𝗟𝗲𝘃𝗲𝗿𝘀

Factor: Recurring Revenue
Impact on Valuation: 5-8X revenue (vs. 1-3X for project work)

Factor: Gross Margins
Impact on Valuation: <50% = 🚩; >70% = ✅
Factor: Customer Concentration
Impact on Valuation: >30% from one client = 20-40% discount

Factor: Management Depth
Impact on Valuation: No second-in-command? 30% valuation hit
Red Flags That Scare Buyers

❌ Inconsistent financial records
❌ Founder = "Key Person" risk
❌ Pending lawsuits/IP disputes
❌ Declining YoY revenue
Your business is your biggest asset

Build it to sell from day one

Even if you never plan to

♻️ Repost if this changes how you think about building businesses

Follow Nathan Hirsch for more lessons from my exit

Get 1 weekly business advice from me here: nathanhirsch.com/newsletter/Image

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More from @NathanHirsch99

Aug 23
10 management fails that bankrupt companies.

(WeWork ignored #1).

Bankruptcy rarely happens overnight.

It follows predictable leadership mistakes.

Avoid these or face collapse.

Save your business now.

Spot them early → save your company: Image
1. Ignoring Cash Flow

Failing to track burn rate, receivables, and operating expenses monthly.

Fix: Run weekly cash forecasts + slash non-essential costs immediately.
2. Scaling Too Fast

Hiring/expanding before validating unit economics (CAC > LTV).

Fix: Freeze hiring until profit per customer exceeds acquisition cost.
Read 12 tweets
Jul 26
Career ceilings exist because we ignore invisible rules.

Master these brutal truths or remain stuck indefinitely.

Hard work guarantees nothing.

Visibility and strategy drive real progress.

Here are 7 things you needed to know yesterday: Image
1/ Your Hard Work Alone Won’t Get You Promoted

Visibility > Effort. Quiet grinders get overlooked.

Build relationships with decision-makers.

Track and verbally share your wins in meetings.
2/ Most Feedback Is Useless Fluff

Vague praise/criticism (“Great job!”) teaches you nothing.

Ask, “What’s one thing I should start, stop, and keep doing?”
Read 8 tweets
Jun 27
Most people struggle to sell.
But the best can sell anything to anyone.

I've been selling for 15+ years now.
Sold Amazon, bookkeeping, SEO.

It’s not about the product.
It’s about psychology, persuasion, and trust.

Master these, and you’ll never be broke.

Here’s how it’s done: Image
1/ Understand Your Audience

Research & Segmentation:

• Identify demographics, psychographics, and behavioral traits.

• Develop detailed buyer personas.
Discover Pain Points:

• Pinpoint challenges, needs, and desires your prospects face.

• Use surveys, interviews, and market analysis.

Tailor Your Message:

• Adapt your approach based on audience insights.

• Customize language, tone, and offers.
Read 14 tweets
Jun 16
Most new business owners make these 8 critical financial mistakes.

Profit isn't the problem; cash flow and chaos are.

Spot these early or pay the price.

8 deadly traps with instant fixes: MN1 Infographic
1. Blurring Personal & Business Funds

Using one account for both transactions.

Jumbling expenses, leading to tax-time chaos.

FIX:

Open separate business accounts + use tools like QuickBooks.
2. Ignoring Cash Flow

Focusing only on profit, not liquidity.

Letting unpaid invoices pile up without follow-up.

FIX:

Run weekly cash flow forecasts + automate invoice reminders.
Read 10 tweets
Jun 13
Toxic culture destroys more teams than anything else.

These 11 signs mean your best people are already leaving.

High performers flee before others notice.

Morale decays in whispers, not explosions.

Spot these before talent leaves: Image
1/ High Turnover (The Revolving Door)

Frequent resignations or "quiet quitting."

New hires leave within months.

What to do: Conduct anonymous exit interviews to uncover root causes.
2/ Passive-Aggressive Communication

Sarcasm, backhanded compliments, or silent treatments.

Meetings end with unresolved tension.

What to do: Enforce a “direct but kind” communication policy.
Read 13 tweets
Jun 2
You fail as an entrepreneur if you can't sell your vision

Jeff Bezos didn't start Amazon to sell books, he sold the vision of an online world

Richard Branson sold the vision of a customer-centric airline, not just flights

Here’s how to sell your vision with clarity and impact: Image
𝗘𝗹𝗲𝗺𝗲𝗻𝘁𝘀 𝗼𝗳 𝗮 𝗖𝗼𝗺𝗽𝗲𝗹𝗹𝗶𝗻𝗴 𝗩𝗶𝘀𝗶𝗼𝗻

1/ Clarity

Your vision should be simple and easy to understand.

Example: “We aim to make sustainable fashion affordable for everyone.”
2/ Purpose

Highlight the “why” behind your vision.

Show how it solves a meaningful problem.

3/ Passion

Convey your excitement and commitment.

Passion is contagious. let it shine through.
Read 18 tweets

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