Why Great Engineers Fail at Go-to-Market and What One VC Learned the Hard Way
For much of his professional life, Simon thought of himself as what he had dreamed of becoming as a child: an inventor. Trained as a mechanical and manufacturing engineer, he spent 15 years at Apple working on some of the company’s most technically demanding problems, contributing to Touch ID, advanced glass forming, robotic polishing, and 3D scanning. His work resulted in more than 50 patents spanning multiple technical domains.
Today, Simon operates from a very different vantage point. He is a venture capitalist writing first checks into early-stage startups. His transition from engineer to investor was not a departure from engineering but a recognition that building transformative products at scale requires solving business problems as rigorously as technical ones. As Simon puts it, “The business challenge was sometimes just as interesting and just as difficult as the engineering problem we were trying to solve.”
Sabrina Paseman, General Partner, Omni Ventures (Photo: Simon Lancaster)
The Restless Engineer
Simon joined Apple in 2008 during the later years of Steve Jobs’ leadership. Within the organization, he developed a reputation as an expert generalist, someone called upon when new, complex problems emerged outside established domains.
“I was always restless,” Simon recalls. “I was always seeking new projects, new ideas, new concepts.” Rather than pursuing narrow specialization or an academic path, he moved across disciplines, applying first-principles thinking to unfamiliar challenges. “I never really became the world expert in anything,” he says. “What I loved was creating novel ideas and innovation.”
As his career advanced, Simon began to question the limits of individual contribution inside a large organization. That curiosity led him toward open innovation, where he worked with suppliers, vendors, and startups to solve problems Apple could not address internally at speed.
Discovering the Complexity of Business Development
Working closely with startups exposed Simon to a different kind of difficulty. Beyond the technical challenges were business problems that demanded creativity and judgment. How could a global corporation become the first customer of a small startup without overwhelming it? How could intellectual property, exclusivity, and investment rights be structured without destroying the company’s future?
“I was always trying not to kill the startup,” Simon says. “I have a heart and a soul, and I felt those problems were sometimes as hard as the technical ones.”
These experiences reshaped his understanding of innovation. Engineers, he observed, are trained to sell features, while markets buy value. “Engineers are not taught to think value first,” he notes. “We’re taught specifications, features, and performance.”
That gap between technical excellence and market relevance would later become central to his investment philosophy.
From Builder to Backer
After leaving Apple, Simon joined one of the startups he had previously evaluated and took on a business development role, selling directly into enterprises. The experience reinforced his belief that go-to-market execution, particularly in deep technology, is among the hardest problems startups face.
Reflecting on this transition, he says, “I realized that the business development problem required just as much innovation as the engineering problem.”
As he began angel investing and mentoring founders, Simon found the work deeply fulfilling. “The time I spent with founders after work hours was some of the most enjoyable moments of my life,” he recalls. Venture capital offered a way to scale that engagement and turn it into a profession.
Rethinking Founder Quality
Simon’s early investing instincts were shaped by his engineering background. Initially, he placed primary emphasis on technical depth. Over time, that changed.
“Great technology is table stakes,” he says. “Of course I will only invest in great technology, but the founding team has to be commercially minded.”
One of his most consistent pieces of advice to founders is blunt: “Speak to a hundred customers before you speak to an investor.” The goal is not early revenue, but evidence that the team understands customer pain, value creation, and buying behavior.
Simon has become particularly attuned to how difficult business development is for technically trained founders. “It’s very hard to get engineers into a mindset where they sell value and not features,” he explains. “I tell founders this almost every day. Stop selling the features of the product.”
As a result, he now favors balanced founding teams, often pairing an extroverted, commercially oriented CEO with a deeply technical CTO.
Can Sales Be Taught
While Simon and his firm provide mentorship to portfolio companies, he is pragmatic about its limits. “You can mentor skills,” he says, “but you can’t really teach personality traits at venture speed.”
In his view, qualities such as communication ability, empathy, and persuasion are foundational. “It’s not even skills,” he emphasizes. “It’s traits.”
This belief has led him to focus on backing founders who already demonstrate strong commercial instincts rather than attempting to transform them post-investment.
Go-to-Market as a Competitive Advantage
Investing primarily at the pre-seed stage, Simon’s firm writes first checks and builds conviction before market validation exists. While the firm is US-focused, he closely observes innovation hubs in Asia, particularly in manufacturing technology.
Across regions, he sees the same pattern. Technical innovation is widespread, but commercialization capability differentiates outcomes. “Sales is already difficult for fluent English-speaking engineers,” Simon notes. “Add a language and cultural barrier, and it becomes even harder.”
For that reason, his firm looks for early signals that founders can engage customers, articulate value, and conduct business development effectively in global markets.
Building a Focused Venture Firm
Simon’s approach to venture capital reflects his belief in focus. Rather than building a generalist fund, he deliberately chose manufacturing technology as a narrow domain.
“The more generalist you invest, the more diluted your strategy becomes,” he says. By contrast, a clear niche creates memorability and credibility. Founders know where to find the firm, and limited partners with aligned interests recognize its value.
Venture Capital as Sales
For those considering starting a venture fund, Simon offers advice that mirrors his views on startups. “At least 50 percent of venture capital is sales,” he says.
Venture capitalists sell portfolio companies to future investors and sell themselves to limited partners. “As an emerging VC, you are the product,” Simon observes. Trust, credibility, and long-term relationship building matter more than transactional fundraising. “My biggest learning,” he adds, “is not to ask for money.”
The Engineer’s Expanded Role
Simon’s journey from engineering to venture capital reflects an expanded definition of innovation. Building advanced products is only the first step. Impact is realized through commercialization, adoption, and scale.
For engineers considering broader roles, his lesson is clear. Technical excellence opens doors, but market understanding determines outcomes. As Simon’s career demonstrates, innovation does not end with invention. It begins there.
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