You’re a founder. The company you’ve built with love and sleepless nights , the dream that eclipsed relationships, family, and travel, is entering its final chapter. Greatness is no longer possible for this company. It won’t ascend to the top of its field, earn public accolades, or see its name emblazoned at the New York Stock Exchange.
You’ve accepted the reality that an aspirational exit will not happen. The best you can hope for now is for another company to buy your business for enough money to take care of your customers, employees, investors, and you.
Or, as it’s commonly known in startup circles, it’s time to land the plane.
You thought it was lonely before?
Sixty-seven percent of startups never return their invested capital. Most fall short of the vision their founders, employees, and shareholders once shared. But few talk about what it feels like for the founder when that realization hits and becomes common knowledge. Never will a founder feel more alone.
Sure, the stakeholders will say the right things. Key employees will promise, “We’re with you to the end.” Truth is, income uncertainty may drive them elsewhere. Investors will claim relationships first and investments second, but suddenly they don’t return calls as quickly.
The board, once hyperinvolved, becomes a shell of itself: attendees barely prep for formal meetings, barely hiding that their attention has moved to the rest of their portfolio.
Soon after you accept that no new capital is coming and no business re-acceleration is plausible, you begin the search for a buyer. And for most founders, that’s uncharted territory.
You’re talking to corp dev pros who negotiate for a living, and they’re better at it than you. You’re fielding questions about price and deal terms you don’t fully understand. You’re managing investors and board members with differing incentive structures. You might be facing debt holders threatening foreclosure or investors enforcing liquidation preferences. Board members may resist a management carve-out (or worse, you don’t know that you need one). Your lawyer might be demanding payment before further work. Or employees are asking whether their options will have any value.
All the while, you’re facing the reality that your own ownership is likely worthless, and your below-market salary feels smaller than ever.
If this all sounds bleak, that’s because it is.
Founders love to build. Learn. Grow. They thrive on experimentation, improvisation, and the climb up an impossible hill. Even tiny wins are enough to fuel the next ascent.
But that’s no longer the game. You have a company nearing the grave, with one low-probability but not impossible task ahead: find a buyer.
A buyer who will likely have all of the leverage. A buyer who might lack founder empathy. At the same time, the people you’ve emotionally relied upon for years, investors, board, employees, customers, begin to quiet quit in front of your eyes.
Is there a happy ending to this story? No.
Can there be an OK ending? Absolutely.
A founder who can land the plane can truthfully say they sold a venture-backed startup. Despite what tech blogs would have you believe, that is a rare feat. Beyond the story, the founder often walks away with something, because investors and boards know the truth: no founder, no deal. Buyers need the founder to integrate the team, customers, and technology. So there is an economic benefit to the founder and the core team for landing the plane safely.
But like every other part of the CEO journey, it’s a skill to be learned.
How to Land the Plane
The lazy answer: Hire a banker.
The truth: Most startup exits aren’t big enough to attract good bankers. Sub-$25M (sometimes sub-$10M or $5M) deals rarely meet the threshold, and giving up a large percentage to a banker makes investor and board approval even harder.
Great bankers earn their keep. They can bring new buyers to the table, create bulletproof diligence materials, and out-negotiate the sharks on the other side. But engaging a banker takes time and cash. For small exits, the math doesn’t always work.
Instead, we teach our founders to do what a banker would do. And we’ve helped land many planes.
What You’ll Need
- Introductory deck. Explains the company and the opportunity.
- Confidential information memorandum (CIM). Covers the business, economics, market, clients, team.
- Financial model. Something straightforward and grounded in historical actuals that is flexible enough to be adjusted based on the type of buyer in front of you.
- Due-diligence data room. Financial statements, engagement metrics, customer waterfall, legal docs, cap table, formation documents, board decks.
- Dedicated deal team. A small number of people in and outside of your company who touch finance, people, product, and legal to prepare documents, review materials, and take meetings along the way. This improves decision-making, gives the CEO leverage, and, importantly, makes the CEO feel a little less alone.
The Sequence
- List creation. Combine management interviews and research to identify target companies and points of contact. Consider acquisition history, balance sheet strength, performance, and relationship quality.
- Initial outreach. Founder-led, ideally to target CEOs. Brief write-up, minimal info shared (blurb + deck only).
- NDA and CIM. A subset of interested targets signs NDAs and receives the CIM.
- Calendar expectations. Set clear dates for initial indications of interest (IOIs), final offers, and decisions.
- Expanded diligence. Targets that advance gain access to broader data, followed by lengthy meetings with management to contextualize the data and imagine a combined future.
- Negotiation. Receive terms and pricing; balance deal completion likelihood against valuation.
- Exclusivity and closing. Final bidder enters exclusivity; aim for a mutually agreed-upon close date. Post-signature diligence will be mostly confirmatory (but not entirely).
Pro Tips
- Skip the games. The shorter your cash runway, the less posturing you can afford. Every founder says, “We have inbound offers.” Every acquirer hears, “They’re dying; let’s get this at outlet prices.” Say plainly that you’re seeking a transaction by a specific date, or you’ll wind down. Your only real leverage is multiple bidders.
- Runway = leverage. Stop spending money on anything that won’t create value within your sale timeline. Runway is your friend and the closer you can be to cash flow positive, the more attractive you’ll be to suitors
- Know your rules. Understand how decisions are made in your company. Most founders don’t. Check your bylaws and voting rights. Who approves a sale? Who can veto? What votes do you need?
- Get ahead of carve-outs. If the exit will fall below the preference stack (meaning common shares won’t see value), get ahead of the carve-out conversation. You and your investors are aligned, and no one wants a zero. Send a short note proposing a fair carve-out (e.g., 10% of proceeds for the team) and get written thumbs-up before you go to market.
- Make engagement easy. Let investors and potential buyers nibble. Don’t block progress with deal-breakers before you’ve even seen an offer. Regardless of the diligence ask, find a way to say yes.
- Don’t negotiate live. They likely are better negotiators than you. Async is your friend. When a buyer floats terms verbally, don’t negotiate on the call. Instead, say, “I’m really excited about the possibility of teaming up. I’m not alone in this decision, so I need to share the terms with my stakeholders. If you can send over a formal document, I’ll circulate it and get feedback right away.” That simple line can turn talk into action and even the playing field.
Grace in the Descent
Everything about launching, growing, and scaling a startup is hard and lonely. But at least you’re climbing a mountain. The climb feeds motivation.
However, when you realize the climb is over, and it’s time to put the company down, that’s when true loneliness sets in. Employees look for new homes. Investors write you off. Board members go silent. Your support network moves on.
But you haven’t.
You still care to finish well. You want to find a home for your customers, your team, your investors. You want to honor your fiduciary responsibility to your shareholders and your years of work with an outcome that, while imperfect, is one you can live with. You want to land the plane even while everyone around you reaches for their parachutes.
A Softer Landing
This stage isn’t fun. It feels more like professional hospice than business building. But even one knowledgeable, empathetic voice can help.
If this is where you are, send us a note. We’re happy to talk through your circumstances and see if we can make this chapter a little less painful, and perhaps a little more satisfying.
For those who want an in-depth handbook on what it means to sell your startup, whether from a position of strength or desperation, our primer is here. Sometimes it’s not about landing the plane but enticing a great exit when a founder has time and leverage. And, if you want to talk through your specific circumstances, we’re happy to gift you an hour of our time.