How to Sell Your Business When Low On Runway

.

Want to sell?

Let's start at the end. You’ll want 3 good offers. That gives you a sense of the market and some leverage. More than 3 is fine but starts to get unmanageable. If you're unresponsive to one because you have so many others, that one might walk away, even if it's your favorite. Having two is risky, but better than one, which is better than none but comes with no leverage.

You need time to do this right. If you have <3 months, it’ll be rushed. You likely won’t get a great outcome, but you might get something. Offers take a month. Closings take 2. Don’t wait. Just start.

If you can buy time, do it. Cutting costs, running lean, using tools like Skyp.ai to replace SDRs and speed up strategic outreach to acquirers or partners—these can help stretch cash and give you options. One company I invested in sold to eBay months after letting all the staff go. A famous founder did the same back in the early 2000s. Remember Blogger? Evan Williams was down to being the only “employee” when Google bought it. Quite the outcome!

So, assuming you have ~3 months and something worth selling, here’s the playbook. 

1. Leverage your connections

Your board, investors, and friends-of-the-company are crucial helpers in getting you high-trust meetings quickly. Focus on CEOs or functional leaders (CPO/CTO). Corp dev will talk, but they rarely push deals forward. If you are a truly deeptech company, Google and companies like it will take unsolicited emails and will likely take a look. Don’t expect much this way, but it is very easy. 

Investment bankers won’t represent you, because the most in-demand don’t do firesales, and the less in demand charge high retainers you shouldn’t (or cannot afford to) pay. But bankers will still introduce you to buyers. They want to look helpful to their contacts, and they know you’ll remember them next time.

Advisors are underrated. Lawyers typically do not give business advice. Board members have fiduciary constraints. Some angels may help, but have conflicting incentives. A good advisor (like me, or others—ask around) has no horse in the race and can guide you. Expect a retainer (up front–after all, you're almost out of cash) and a success fee that’s substantially less than banker fees. To bring on an advisor, however, you’d likely want to have one or two interested buyers. Your VCs or others in your network will likely have recommendations to this sort of person. 

2. Get an offer

You need a signed LOI with 2 months to spare. Oral offers or conversations aren’t enough. Even for an acquihire—get it in writing. A tight timeline doesn’t allow for the kind of miscommunication or assumptions that come with not writing things down. 

Ideally, you get a preemptive offer. If you’ve built relationships you might generate inbound interest.

That’s what happened to me: I met a competitor CEO who had just raised a war chest. He asked if we were open to being acquired. I pretended to be only slightly interested, even though I was desperate. Three weeks later, we had an LOI.

If that’s not happening, you run a process. Talk to ideal buyers. Be honest: you’re low on cash, and need to decide in 90 days. If they’re interested, they’ll move. If they’re not, no amount of spin will change it.

Here’s the email I suggest:

Hi {CEO},

We’re low on cash and expect to decide next steps within 3 months. Your company is my top choice for where we’d land because {concise, specific reason}. Do you have 30 minutes to chat this week?

— {Your Name}

If you get real traction, you can spark FOMO by telling others you have a pending offer (but don’t lie). That only works if they believe you.

Use tools like Skyp.ai to automate outreach and follow-ups, especially to targets you don’t have warm intros to. It’s one of the rare use cases where AI in GTM can drive real ROI fast: outbound for M&A interest.

3. Land the plane

A signed LOI is just the beginning. It might take 2 months to close—or more. Delays are normal. Budget for them.

Whatever you do, avoid taking a loan from the acquirer. It's a trap. Debt comes with recourse, so there are a variety of scenarios if you take debt from your acquirer, where they don't acquire your company, but get its assets anyway. Unless you have no other option, don’t do it. Manage cash tightly: keep payroll going, pay only the most essential expenses, and defer the rest.

While you’re landing the plane

First, there will be turbulence as you land the plane. Many planes that look like they’ll on a clear approach end up crashing. For example, one friend’s startup had an LOI from Twitter. Then Elon bought Twitter, and immediately killed all M&A deals in progress. Another had a board member try to renegotiate the deal at the last minute, and the delays that caused killed it. A third was in talks with a company when its CEO unexpectedly died on vacation. He actually got that deal done, but it was a very close thing. In my own experience, one board member refused to take a deal because he wanted more money, but we couldn’t get it from the acquirer. Eventually, the company had to shut down. 

Second, if you keep any significant part of your team around, you need to give them something to do. The best scenario is that you have a business for them to run. Keep running it–maybe even try to grow it. Tools like Skyp, which does AI-powered cold outbound, can be more affordable than a full time hire but as effective. It’s fine to experiment at this stage–after all, if something hits, and you turn things around, that can be a huge selling point. If you don’t have a business, these experiments can be how you create excitement for your buyer while keeping your team engaged. (If you’re navigating this with a partner like Thunder, even better. A focused sell-side process can widen your buyer pool and avoid wasted cycles—but you still need to be realistic about time.)

Third, consider how much of your team you need. One friend ran a large, top-VC-backed company and had 100 employees. They started a process and realized quickly they weren’t going to get offers they wanted. While they planned some cuts, they increased that and reduced the team size to 12 people. Suddenly, they were profitable. They automated much of their existing business, and invested those profits in a pivot–instead of taking an insulting M&A outcome.

The most important aspect is for you, the founder/CEO, to stay focused on landing the plane. I remember running a competitive process once where the head of product asked, “Is everything we’re doing optimizing our M&A process?” She was upset because we had blown up the product  roadmap to address something that had come up in diligence. And the answer was an unequivocal “yes!”

Final thoughts

Selling a startup, even quickly, is complex. But the first step is emotional: accepting that the current company is not going to be the breakout you had hoped. That frees you to make decisions with clarity.

And if you can buy yourself time, do it. That means cut costs. That means not doing things you’ve maybe always done, or replacing people with AI. Skyp instead of SDRs, Fin for customer support, ChatGPT or Claude instead of analysts. And—act quickly. 

While you’re landing the plane is not the time to be setting up your landing. It may be too late for you if you’re at this point but if you’re not–avoid being in this situation. The best kind of fuel for your entrepreneurial journey is customer revenue! Get more of it, quickly, so that if you do choose to sell, you can do so from a position of strength. 

The founder I mentioned at the start got close to selling, but didn’t. A year later, he felt good about it. He’d run a clean process. That’s worth a lot.

Every great founder has one of these stories. We just don’t talk about them enough.

PS This is not legal advice. Just my experience

.