Why Technical Founders Fail at Sales

The late-night text message lit up my phone:

"I just can't do this sales thing. I'm an engineer, not a salesperson."

This came from a brilliant developer friend who had quit his job six months earlier to build a SaaS product. He'd created something genuinely innovative, but was now struggling to find customers. His savings were dwindling, and the pressure was mounting.

I've seen this story play out dozens of times.

A talented engineer builds an impressive product, but can't make the leap from building to selling. The product languishes, and the business eventually fails—not because the technology was bad, but because not enough people knew about it or understood its value.

I was reminded of this pattern during my recent conversation with James Green on the Product Driven podcast. James is the General Partner and Co-founder of DQ Ventures (which stands for "Don't Quit," not Dairy Queen as I initially thought). His fund helps aspiring entrepreneurs turn their ideas into viable businesses.

The Hard Truth About Entrepreneurship

During our conversation, James shared something that might be uncomfortable for many technical founders to hear: entrepreneurship is fundamentally about sales.

Unless you're building the next Facebook or Instagram that grows virally, about 90% of your job as a founder is creating a value proposition and finding people who want that value. In other words, selling.

Many of us read about unicorn startups on TechCrunch and imagine a fantasy scenario:

1. Build an amazing product over a weekend

2. Set up a marketing site with AI on Monday

3. Make one post on Twitter and LinkedIn on Tuesday

4. Watch it go viral on Wednesday

5. Raise $10 million in Series A funding on Thursday

James and I had a good laugh about this fantasy because we've both seen the harsh reality up close. The truth is messier and more difficult.

Why We Engineers Struggle With Sales

I've always been a builder at heart. When I founded Stackify in 2012, my background was as a CTO and engineer—not a salesperson. I hired salespeople, tried various marketing tactics, but it was a brutal learning experience.

One insight I shared with James is how deeply engineers struggle with context switching between building and selling. When I'm writing code, I become completely absorbed. I described it to James like this:

"When I'm writing code, I'm like a dog with a bone. That's all I can think about day and night. It's like building an IKEA desk or putting together a Lego set—until I finish, I can't think about anything else."

Imagine building that IKEA desk halfway and then stopping to make sales calls. It feels impossible. The problem is, with software, the desk never gets finished. There's always more to build, more to improve, more features to add.

This is why technical founders often default to building rather than selling. It's simply how our brains are wired.

The Mental Shift That Changes Everything

The breakthrough comes when you realize that selling isn't what you think it is.

Selling is actually listening. It's not speaking. If you're a good salesperson, you're listening 80% of the time.

James shared: "I think that is actually problem-solving as well. You're not actually giving up the problem-solving part of your job. You're just solving the problem by really understanding what that problem is."

This reframe was powerful. We're not "selling" in the pushy, aggressive sense that makes many of us uncomfortable. We're problem-solving through conversation.

Think about it: as engineers, we love to understand problems and figure out solutions. Sales is just doing that verbally with potential customers instead of doing it in code.

How to Bridge the Gap

If you're a technical founder who breaks into a cold sweat at the thought of selling, here are some approaches that have worked for me and other engineers I've mentored:

Think of it as sharing your creation, not selling it

Don't be scared to talk about what you've built. Think of it as showing people your cool creation—just like you'd show off that IKEA desk to your family.

I told James: "I built this thing and I just want to go tell people about this cool thing that I built. Who doesn't want to do that?"

Even if it's just on LinkedIn, tell people, "I built this thing. Here's why I built it." People will be excited because you're excited.

Seek feedback, especially negative feedback

Many technical people avoid customer conversations because they fear criticism. But that's exactly what you need!

James pointed out that you want someone to tell you if your product isn't working for them, so you can understand why and improve it. Early negative feedback is infinitely more valuable than silence.

Redefine what sales means to you

Instead of thinking about "closing deals" or "hitting targets," think about having conversations to understand problems.

When you approach potential customers, don't ask them to buy. Instead, say something like: "Can you just tell me what you think of this? It could be bad, it could be good."

If they respond, "That's cool, but can you make it work like this instead?" then you've got valuable feedback and potentially a sale without ever having to do traditional "selling."

Use your technical expertise as an advantage

Technical founders often make excellent salespeople once they get over the initial resistance. Why? Because nobody wants to be sold to by a slick salesperson with no substance.

People want to have a conversation with someone who deeply understands their problem and can genuinely help solve it. As a technical person, you have that depth of understanding.

The "Don't Quit" Strategy for Technical Founders

James's fund, DQ Ventures, specializes in helping entrepreneurs keep their day jobs while building their startups on the side. This dramatically decreases risk and gives you runway to figure out product-market fit before going all-in.

I'm a huge fan of this approach. My first company, which I founded in 2003, started as a side project. I kept my full-time job as a software developer in a medical lab for as long as possible, eventually negotiating to work 30 hours a week (6am to noon) so I could spend afternoons on my startup.

That company eventually grew to $35 million in annual revenue—all bootstrapped, no venture capital.

The Reality Check

The biggest myth in startups is "build it and they will come." That's a fantasy that has killed countless promising startups.

The reality? About 95% of tech startups fail, and many of those failures happen because technical founders build products that nobody knows about or wants to buy.

If you're a technical founder who has been avoiding the sales side of your business, it's time to face it head-on. Reframe it as problem-solving, start small, and remember that your technical expertise is actually a sales advantage.

The journey from engineer to entrepreneur requires expanding your comfort zone. But once you make that leap, you'll have unlocked the most critical skill for startup success.

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