Love and exits: what dating and selling your business have in common

Most of us keep a clear line between our personal and professional lives. Performance reviews and video calls go in one basket; dating, nights out and jokes in the other. For the next few minutes, let's remove that line, and look at why succeeding at dating and succeeding at selling your business take a remarkably similar set of skills.

PrologueTwo true stories

As kids at Mount Temple school in Dublin, Alison Stewart met Paul Hewson, a boy in the year above. A few years later, while he was starting a band with some school friends, they began dating. Hewson became Bono, the band became U2, and the two married in 1982. They're still together.

Decades later, in the American Midwest, a scrap metal dealer bought a small gold egg at a market for about $13,000, planning to sell it for its metal. Years later, he searched online for the name engraved on it and found an article about a lost Fabergé egg made for the Russian imperial family. An expert from a London jeweller came to check it. It was the real thing, valued at around $33 million.

What do they have in common? You shouldn't plan your life around either. Marrying your school sweetheart and finding a masterpiece in a scrap heap are both extraordinary exceptions. For most of us, success in love and in business looks very different: we have to work for it. The good news is that the skills for finding love and for selling your company in the real world are well within reach, if you take the right approach.

Chapter IPreparation

The first thing any dating coach tells a client is to value themselves before expecting anyone else to. That doesn't mean being fake: it means bringing out the best of the real you. A job you enjoy, stories worth telling, clean clothes that fit, a flat that smells good.

In both love and business, first impressions matter. Nobody knows your business better than you, and it's up to you to show the value you've built, in the most favourable and honest light. And because buyers want both profit and growth, the time before a sale is your chance to improve both. If you run a software business, SaaS due diligence: 10 things buyers check shows what buyers will look at.

Chapter IIProximity

Whether you're looking for a partner or a buyer, getting out there and meeting people is the best way to find what you want. Psychologists call it the proximity effect: the more often people come across each other, the more likely they are to like each other. Robert Zajonc found the same with what he called the mere-exposure effect: the more we're exposed to something, the more positively we tend to see it.

That translates directly to selling your business. A good advisor can introduce you to potential buyers a year or more before you're ready to sell. Those conversations give you useful feedback, and let the people who matter in your market get to know you over time.

Familiarity builds trust, and trust makes buyers more willing and motivated. A sale usually involves long negotiations, and the more a buyer trusts that you're negotiating in good faith, the less defensive they'll be.

Trust goes both ways. You'll probably stay tied to your buyer after the sale in at least one way: a transition period, an earn-out over several years, or shares in the buyer as part of the price. Each of these can go very badly with the wrong buyer. The more buyers you meet, the better you get at telling who you can trust.

Chapter IIIFinding your match

Anyone who has spent five minutes on a dating app knows the challenge isn't finding the perfect match: it's working out who to talk to in the first place. There's an ocean of buyers out there, from family offices and private equity funds to roll-ups, strategic buyers and even competitors, all looking for different things at different times. Narrowing the pool to the ones who could be a real match is one of the main things an advisor brings.

As you move into this phase, know what you want, and be open about it. Matchmakers ask clients to build a profile that screens for what matters to them: if your three golden retrievers are the centre of your world, say you're looking for a dog lover. In a sale, important questions will come up. Know where you stand before you're asked:

• how long you're willing to stay with the company after the sale
• what you want for your team and your brand
• what you're looking for in a buyer: knowledge of your industry, a track record of acquisitions, and the money to close
• what price you want, even if it feels uncomfortable to say

Being open doesn't just filter out the wrong buyers: it attracts the right ones. Research on couples finds that partners tend to be alike in age, background, education and outlook. A sale is a two-way process too: interview buyers as much as they interview you. And when offers come in, compare the whole offer, not just the headline price: how much you get at closing, how much depends on the future, and how certain the buyer is to close.

Remember that the people across the table are human too. They have their own criteria, targets, and bosses or investors to answer to, and many look at hundreds of companies a year. The more honest you are about what you want, the better your conversations will be.

Chapter IVBeing intentional

It makes sense that selling your business and finding a partner have so much in common. Both mean putting something you love out into the world, whether that's yourself or the company you built. Both involve strong emotions: ambition, passion, apprehension, trust and hope. And both are decisions that can change your life.

As the saying goes, luck is what happens when preparation meets opportunity. A few people will keep finding true love at school, Fabergé eggs in scrap heaps, and record multiples on their exits. For the rest of us, the key is being intentional: having a plan, and following it until the right opportunity comes along.

Last updated July 2025 · Written by Christian Bax, Nextoria