The late Steve D. Sims didn't build his career by going to the right schools or knowing the right people... He built it by figuring out, one conversation at a time, exactly how successful people think — and then doing what they do.

Born to a blue collar family and starting work as a doorman at nightclubs in East London, Sims eventually became the founder of a high-end concierge business that closed down museums in Florence for private dinners, sent clients to the wreck of the Titanic, and put him in rooms with everyone from Elton John to Elon Musk. Forbes and Entrepreneur magazine called him "the real-life Wizard of Oz."

He was also a 2-time bestselling author — Bluefishing: The Art of Making Things Happen and Go for Stupid: The Art of Achieving Ridiculous Goals — and a sought-after keynote speaker who spoke at audiences at Harvard and the Pentagon.

In an podcast interview with the Business Acquisition Summit’s Expert Interview Series, Sims broke down the relationship and communication principles that quietly drove everything he built. For acquisition entrepreneurs, dealmakers, and anyone trying to get further faster, the lessons are immediately actionable.

Here are 7 of his most powerful insights:

Early in his career, Sims made a habit of approaching wealthy, successful people and asking the question he thought would unlock everything: "How come you're so rich and I'm not?"

It didn't work.

The question pointed people toward money, and all he got were monetary answers — stock portfolios, inheritance, luck.

He tweaked it to "How come you're so wealthy?" and got something different: stories about finding God, meeting a spouse, having children… Meaningful, but not so actionable.

It took him nearly 4 years of iteration before he landed on the right framing: "How come you're so successful, and so many others are not?"

That question unlocked everything.

It sent people into the goal-achievement part of their thinking. They started sharing how they viewed time, relationships, and opportunity. Sims walked out of those conversations and immediately started implementing what he learned.

The takeaway for dealmakers: The quality of information in any negotiation, due diligence conversation, or seller meeting is often determined by the quality of the question. Before the next important conversation, spend time crafting the right question — not just the obvious one.

Sims used a simple game to illustrate how most people approach relationships the wrong way. Imagine someone invites you to a Saturday barbecue. What's the first question that comes to mind?

For most people it's one of these: Who's going to be there? What should I wear? Can I bring someone?

All of those questions are about what the event can do for them.

Sims argued the first question should always be: "What can I bring?"

He called it the Barbecue Mindset, and he applied it to every professional relationship. Before walking into any room — a networking event, a seller meeting, a first call with an investor — the question isn't what do I need from this person? It's what can I contribute to them?

When Sims wanted something from someone with influence, he didn't lead with the ask. He led with introductions, opportunities, referrals, and visibility — building what he called a "credibility bank." By the time he mentioned his own needs, the other person was often already looking for ways to return the favor.

When Sims described himself as "selfish," people laughed — because they've been taught since childhood that selfishness is a character flaw. He pushed back hard on this.

His point: on every commercial flight, the safety briefing instructs passengers to put on your own oxygen mask before helping anyone else. No one argues with that. The same logic applies to building knowledge, skills, and value.

Sims spent years relentlessly improving himself — absorbing lessons from successful people, implementing what he learned, refining how he showed up — not out of generosity, but out of self-interest. The result was that he became someone worth knowing, and his network followed naturally.

This reframes the question from "how do I get access to the right people?" to "who do I need to become so that the right people want access to me?"

One of Sims' most counterintuitive observations was that the wealthiest, most successful people are almost completely indifferent to money as a motivator.

He made the point simply: if someone approached Elton John and offered $100 to do something, the answer would be no. If they offered $100,000, the answer would still be no. At that level of success, money made while on the toilet exceeds what most people earn in a week.

What successful people care about, Sims said, is impact, experience, and legacy.

This has direct implications for anyone trying to get a deal done, land a partnership, or earn a seat at the table. Pitching terms and financial upside to someone who is already wealthy is often the wrong frame entirely. The better pitch speaks to what they'll be remembered for, what they'll experience, and what they'll build.

Sims identified what he called "The Big C" as one of the most underestimated problems in business today: confusion.

His framework: every audience, every room, every potential client contains three groups. The first group loves you instinctively — your energy, your message, your style. The second group dislikes you just as instinctively. The third group — the fence-sitters — are the dangerous ones.

Most people spend enormous energy trying to win over the fence-sitters. They soften their message, polish their image, choose words carefully enough not to offend anyone. The result, Sims argued, is that they end up saying nothing clearly — and a confused person never pulls out a credit card.

His solution: be so clear about who you are and what you stand for that there’s no room for ambiguity.

Old Fashioned drinks... Motorcycles... Black t-shirts... Pitbull dogs… Blunt honesty... That was Steve — take it or leave it.

For acquisition entrepreneurs, the lesson is this: vague positioning in marketing, outreach, or deal conversations creates friction. Clarity — even if it repels some people — moves things forward faster.

One of Sims' most practical tactics for maintaining relationships over time cost almost nothing and required almost no ongoing effort.

Here's how it worked: when Sims met someone, he paid attention to what they were genuinely interested in — vintage cars, red wine, gardening, whatever it was. He then found a relevant magazine, negotiated a group discount (most publications will offer 40% or more for bulk subscriptions), and subscribed that person to it.

Three or four times a year, the magazine landed on their doorstep. Every single time it did, they thought of Sims. He got a text message. A conversation started. A relationship that might otherwise have gone cold stayed warm — with no active effort on his part between issues.

He called it “outsourcing the relationship.” The result was that people regularly reached out to him feeling like they had re-initiated contact, when in reality the trigger was a $20 subscription.

For dealmakers with a network of potential sellers, capital partners, or referral sources, this principle scales easily... A relevant book, a local event invitation, or a well-timed industry article can do the same type of work.

Sims had a provocative take on branding: he wished the word didn't exist.

His definition: branding is the conversation people have about someone when that person is no longer in the room. And whether anyone actively manages it or not, that conversation is already happening.

The alternative he preferred wasn't "branding" — it was transparency. He argued that the most effective thing any professional can do is show up the same way everywhere, say what they actually think, and stop trying to be palatable to everyone.

When someone asked him how his day was going and it had been rough, he didn't say fine. He said it was rough, and here's what he was dealing with. That kind of directness, he noted, is immediately disarming. It makes people trust faster than any carefully crafted persona ever could.

For acquisition entrepreneurs, this matters in seller conversations especially. Sellers can sense inauthenticity. But when a buyer shows up as exactly who they are — clear about their strategy, honest about what they're looking for, transparent about how a deal might work — it builds more confidence than a polished pitch.

Steve Sims built one of the most unusual careers in business by doing something remarkably simple: figuring out what successful people actually do, doing it himself, and leading every relationship with value — rather than need.

None of it required starting capital, an Ivy League degree, or a warm introduction...

It DID require curiosity, discipline, and the willingness to show up as exactly who he was, even when that made some people uncomfortable.

For anyone in the business of finding deals, building partnerships, and earning trust from strangers, that's about as simple & actionable a blueprint as it gets.

Note: Steve sadly passed away from cancer in 2025. As demonstrated by this email, he has an inspiring legacy which continues to make a big impact. Let’s take a page out of his book by living life to the fullest... Deal?

Thanks for reading Acquiring & Exiting.