Two years to close one deal

I love driving through mountains. There's something about winding roads that clears my head — the curves, the elevation changes, the way you can't see what's around the next bend. It's where I do some of my best thinking.

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A few weeks ago, I was driving a mountain pass, hands on the wheel, navigating switchback after switchback. And I started thinking: if this was a straight line on the map, it'd be 150 kilometers. Two hours, maybe. But the reality? 300 kilometers. Five hours.

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Because the road doesn't go straight. It curves around what you can't see from above. And I started thinking about how many times I've seen this same pattern in business — where what looks like waste from above is actually intelligence from the ground.

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Back in 2012, my first business partner couldn't deliver on sales. We had to let people go. I had to figure out how to find clients myself, fast. So I went to Elance — a freelance platform that eventually got bought by Upwork. Started writing detailed bids for every project, researching prospects, crafting thoughtful proposals. It worked. We got our first clients there, started rebuilding. From 2012 to 2014, it was solid. Long-term clients, real projects.

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At the same time, I started experimenting with LinkedIn. Not pitching services — offering partnerships. I'd message people: "We have developers, office, expertise, portfolio, competitive pricing. Let's build something together." That led to my second agency with a partner from New York. Those LinkedIn conversations planted the seed.

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But by 2014-2015, Elance was changing. Upwork bought them out, and the quality started dropping. More low-quality competitors, more freelancers undercutting on price. We were spending more effort on bids, fighting harder for worse clients. I knew we needed to get off the platform. We couldn't be dependent on one source. That's when I met consultants at a conference who specialized in building sales processes for IT outsourcing agencies like ours. And I thought: email campaigns. That's something we control. No platform dependency. Let's talk to these guys.

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They looked at what we were doing and couldn't understand it.

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"You're wasting time on LinkedIn. Social media? How many messages can you even send? Elance is dying, you're spending hours on custom bids. Email is where you should be. Volume matters. Buy databases, build infrastructure, automate follow-ups, use proven templates. You need clients now."

Made sense. On paper, our approach looked wildly inefficient.

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So we invested. Sent our team to their courses. Hired them as consultants. Built the email infrastructure — multiple domains, warm-up sequences, deliverability monitoring. We were programmers, we thought: this is easy, we'll set it up ourselves.

We did. And it cost us over $50K — courses, infrastructure, databases, team training, consultant fees. Then we launched the campaigns. Tested subject lines. A/B tested copy. Built sequences — not just one email, chains of follow-ups with case studies and industry insights.

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And the results came in.

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"Don't ever email me again." "Where did you get my address?" "I'm reporting you."

It killed team morale. They'd spend hours crafting campaigns and get hostile responses or silence.

Meanwhile, I'd kept a small team — just two people — continuing to work LinkedIn the old way. Personalized messages. Not often. Taking time. Building relationships slowly.

And those two people were bringing in more revenue than the entire email team.

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Not just more leads. More revenue.

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The email campaigns generated responses like "send us your deck, we'll think about it." The LinkedIn team was getting "let's schedule a call" and "when can we start?"

When I calculated the actual ROI — factoring in the infrastructure costs, the database purchases, the consultant fees, the team salaries — the gap was staggering. We were spending a fortune to get worse results.

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I hired a different consultant. This one specialized in social selling on LinkedIn, a term that was just starting to emerge. And he did something the first consultants never did: he studied what we were already doing. He looked at our email campaigns. He looked at our platform bids. He looked at what was working on LinkedIn.

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Then he said: "You're actually doing it right. On the platforms and on LinkedIn. What you've built intuitively is exactly what works. I can help you systematize it so you can scale, but don't change the fundamentals. Your people are comfortable with this approach, you're already seeing positive signals. The only thing you need to understand is this: on LinkedIn, you're not selling services. You're building relationships. And you only sell after trust is established."

That's when it clicked.

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A few years later — after we'd fully committed to the LinkedIn approach and buried email campaigns like a bad memory — we had our monthly strategic call with the sales team. One of our lead gen people was giving her update. Young girl, maybe 23, incredibly talented. LinkedIn had blocked her account seven times because they couldn't believe she wasn't using bots. She was just that active, that engaged, that effective.She was going through her pipeline when she said, almost sheepishly:

"I have a client that just came through. I've been working on him for a while.

"I asked: "How long?"

"About two years. He was one of my first leads when I joined. "

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We almost fell off our chairs. Someone's mouth literally hung open. Two years? For one lead?

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The client was a Canadian company building an app for realtors. She'd been following his profile for two years — not pitching, just staying present. Commenting on his posts. Congratulating him on milestones. Sharing our news when it was relevant, like when we launched a podcast with client interviews. He'd share things too. Where he traveled. When he got sick. It became real.

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When he finally reached out, he told her: "Nobody's ever followed up with me like this. I'm confident my project is in the right hands."We worked with them for years.

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If we'd listened to the first consultants — if we'd gone all-in on email and killed the LinkedIn work — we never would've gotten that client. Because what looked like wasted time from above had reasons on the ground.

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The research? That's how we found real prospects with budgets and pain worth solving.

The relationship building? That's what created trust automation never could.

The long cycles? That showed we understood their world, not just our pitch.

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Those curves weren't inefficiency. They were intelligence.

The consultants saw the map. Not the terrain.

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What I didn't see

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I'd spent $50K learning what they couldn't see from their altitude: the curves in our process weren't waste. They were the path that actually worked. And every time we tried to straighten them, we lost what made it effective.

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I think about this a lot now. How many founders are trying to straighten roads that work because someone told them curves are waste? How many are spending money on shortcuts that make things longer?

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Maybe your process doesn't need to be repaved. Maybe it just needs guardrails on a dangerous section. Lighting on a dark stretch. Or yes, maybe a bridge — but only where the terrain actually requires it, not because straight looks better on paper. The people trying to cut corners and go straight? They're the ones who end up broken at the bottom of the mountain. But you don't repave the whole road just because it curves.

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Here's what I want you to think about:

Look at your process — the one that feels inefficient, the one you keep thinking you should "fix."

Ask yourself: why do we do it this way? Not what a consultant would say. What you know from being on the ground. Maybe there's context no outsider sees. Maybe there's history that matters. Maybe the curve exists for a reason. And maybe all you need is a light, not a bulldozer.

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Here's my question to you, what part of your business looks messy from above but actually works when you're in it? Hit reply and tell me. I'm curious what curves you're protecting.

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P.S. That lead generator? She went on to become the head of our lead gen team. And her approach — slow, relationship-focused, human — became the foundation of how we trained everyone after her. Not because it scaled fastest. Because it worked best.