How to Structure a Deal That Leaves Both Sides Smiling (or at Least Not Suing Each Other)
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How to Structure a Deal That Leaves Both Sides Smiling (or at Least Not Suing Each Other)

Most startup acquisitions are either a dream exit – or a slow-motion disaster. Here’s how to structure your deal like a pro, with no tears.

Indiemaker Team

By Indiemaker Team

Let’s face it: most startup acquisitions go smoother on Twitter than in real life.

One founder wants to retire to Bali and forget their password manager ever existed. The buyer wants a discount, 12 months of tech support, and a lifetime supply of goodwill. The result? A deal that either explodes in a fire or dies in a Google Doc.

If you’re a bootstrapped Indiemaker dreaming of a clean exit – or a buyer sniffing around Indiemaker for your next win – here’s how to structure deals that don’t end with one party rage-quitting capitalism.

🌝 Which Deal Type Fits You? (Quick Flowchart)

💵 1. The Clean Break: Full Cash Upfront

Best for: Sellers ready to ghost. Buyers who are willing to take a risk with their ROI.

  • Seller: Walk away with all the money and none of the headaches. Downside? You’ll second-guess yourself the first time the buyer 10x’s the revenue.
  • Buyer: Congrats, you own a mystery box! Could be gold. It could be legacy code wrapped in duct tape.

Tip: Escrow everything. Get the logins. Don’t forget Stripe, domain DNS, and any customer emails buried in Zapier.

⚠️ Cautionary Tale: One buyer forgot to ask for Stripe keys. The seller stopped responding. Revenue: locked in limbo. Lesson? Get a damn checklist.

💸 2. The Flexible Close: Cash + Seller Financing

Best for: Sellers with patience. Buyers without private equity money.

  • Seller: Get paid over time. Risk: if the buyer tanks it, so does your payday.
  • Buyer: Lowers upfront cost, but you’re on a timer. Screw up, and you still owe money.

Tip: Lawyer up. Use payment milestones, interest terms, and late payment clauses. Don’t “trust vibes.”

⚠️ Storytime: In one indie deal, the buyer missed two payments and ghosted. No contract. No recourse. Just “good faith” and bad decisions.

🌟 3. The Performance Play: Earn-Out + Cash

Best for: Mutual sceptics with something to prove.

  • Seller: Get more if the biz keeps growing. Bad if the buyer tanks the roadmap and blames the KPIs.
  • Buyer: Great for “paying for performance.” Bad if you fudge metrics or get creative with accounting.

Tip: Define KPIs like a startup prenuptial. Be specific: MRR, churn, revenue – tracked with neutral tools.

🔥 Contrarian View: Earn-outs seem fair – until you’re arguing with the buyer about which Stripe refunds “count.” Ask yourself: Do you trust this person with your retirement?

📈 4. The Partnership Play: Equity + Cash

Best for: Sellers who want to fade into the background, not disappear.

  • Seller: Stay passively involved and cash out later (maybe). But remember: minority equity ≠ control.
  • Buyer: Keeps the founder’s brain on call. Can be great – until they start weighing in uninvited.

Tip: Spell out equity terms, dilution clauses, and exit scenarios. Otherwise? Messy divorces.

⚠️ Anecdote: A founder sold 80% of a SaaS, stayed on the cap table... and got diluted to oblivion during a “strategic pivot.” Whoops.

💀 5. The Hail Mary Deal That Probably Ends in Tears: Full Seller Financing + Earn-Out

Best for: Buyers with no cash, sellers with no better offers, and both parties with therapy budgets.

  • Seller: You’re funding your own exit. And hoping the buyer doesn’t crash it into a wall.
  • Buyer: You get the keys for free – if you can drive. But if you stall, the seller might repossess.

Tip: Only do this if you’ve run out of LinkedIn contacts. And for the love of SaaS, get personal guarantees.

🚨 Real Talk: One founder did this with a buyer who “couldn’t afford the first $500 payment” and then blamed ChatGPT for not growing the MRR. You can’t make this up.

🧠 Final Thought: The Deal Structure Is Just the Stage. The Drama Is in the People.

No structure guarantees success. What matters is clarity, trust, and matching reality to expectations, not your fantasy exit tweet.

Deals fall apart because of silence, ego, and “assumptions.” So write everything down. Be honest about what each side wants. And if you’re the seller? Ask yourself: Would I finance this person’s car, let alone my business?

You don’t need a perfect deal. Just one that won’t haunt your Slack memories or bankrupt your patience.

And if you're ready to explore or list your deal, start by finding the right structure. The deal type isn't just paperwork – it's strategy.

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