Podcast Spotlight: Greg Gottesman on AI, Startups, and the Future of Work
This week on AI First with Adam & Andy, we sat down with Greg Gottesman, a longtime venture capitalist, entrepreneur, and co-founder of Pioneer Square Labs.
Greg has spent nearly 30 years building companies, investing through multiple technology waves, and teaching entrepreneurship. Today, almost everything he works on is AI-driven, from startup creation to the idea of an “AI co-founder.”
This conversation wasn’t about tools or hype. It was about what actually changes when AI lowers the cost of creation, and what doesn’t.
Below are the key takeaways leaders should be paying attention to.
Product Is Rarely Why Companies Fail
Greg shared one of the most important pattern-recognition insights from decades in startups:
In almost 30 years, I can count on one hand the number of times a company failed because we couldn’t build the product or figure out the technology.
Instead, companies almost always fail because they can’t figure out cost-effective distribution.
Why this matters now: AI is making product development easier, faster, and cheaper. That doesn’t reduce risk, it increases competition.
Where there used to be 3–4 startups in a category, now there may be 10–15.
The bottleneck has shifted from building to getting adopted.
AI Makes Distribution Harder, Not Easier
As product creation gets cheaper, attention gets more expensive.
Greg pointed out that traditional distribution channels (especially Google and Facebook) are no longer cost-effective for many companies. That reality applies to startups and large enterprises.
The implication: The next wave of innovation won’t come from product features alone. It will come from:
new distribution models
trust-based channels
differentiated access to customers
In an AI world, distribution becomes the moat.
Most Companies Are Still “Human with AI Sprinkled In”
Greg offered a helpful framing for where we actually are today:
Most organizations are human-led, with AI used sporadically
Often AI is delegated to a “crack team” or isolated function
Leaders themselves are not consistently using AI in daily decision-making
This approach limits impact.
True progress happens when every role, including leadership, uses AI as a core capability, not a side experiment.
AI-Native Isn’t Here Yet (But It’s Coming)
While many startups are building AI products, Greg made an important distinction:
Even the most advanced companies today are not truly AI-native.
Today’s reality:
Humans do the work
AI augments, assists, or accelerates
Where we’re headed:
AI does more of the work
Humans review, direct, and oversee
Greg described this future as moving from “humans with AI sprinkled in” → “AI with humans sprinkled in.”
That shift will happen unevenly, faster in startups and tech, slower in regulated industries, but it’s coming.
Leadership Is the Real Constraint
One of the most important themes in the conversation: AI transformation is not a technology problem, it’s a leadership one.
Many CEOs understand AI at a high level but are consumed by urgent, day-to-day realities:
payroll
customers
delivery pressure
The challenge is prioritizing what’s important, not just what’s urgent.
Companies that wait until AI is “fully ready” will be late. Companies that start changing how leaders work now will compound advantages.
Final Thought
AI will likely be more transformative than the internet, even if most AI startups fail.
That’s not a contradiction. It’s how every major technology shift plays out.
The winners won’t be the companies that build the most features the fastest.
They’ll be the ones that:
rethink how work gets done
rethink how customers are reached
and rethink the role humans play alongside increasingly capable AI systems
🎧 Listen to the full episode to hear Greg’s perspective on AI-native companies, startup studios, and what leaders should actually focus on next.
Stay Curious. Stay AI-First.
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