Winning Strategies of Smart Founders in AI

What if you could create a digital version of yourself that delivers expertise 24/7? In today’s AI-driven world, founders are already building virtual “body doubles” that scale their insights around the clock.

AI Body Doubles: Users Tell AI Things They Won’t Tell Humans

Imagine a version of yourself that can answer every question, give feedback on your slide decks, and coach you through your toughest board meetings—all without ever needing to schedule a call. That’s exactly what Jason Lemkin did when he ingested over 20 million words of his own content—tweets, blog posts, reports, videos—and trained an AI clone via a service like deli.ai. By scraping RSS feeds and APIs daily, this digital twin auto-updates 24/7 with negligible hallucinations. It remembers every detail you’ve ever shared—what you said on stage with Sam Altman in 2015 versus a podcast chat last month—so it can connect dots you’ve long forgotten. Founders are using these AI doubles to practice investor pitches, refine sales scripts, even explore personal anxieties in what amounts to a confidential therapy session. Over time, Lemkin found that “users will tell AI things that they won’t tell humans,” unlocking candid feedback on everything from hiring struggles to big-picture strategy.

“Users will tell AI things that they won’t tell humans.”

The Incumbents Are Dying

Traditional software companies that once thrived on multi-year product cycles and 120–130% net revenue retention are now feeling intense pressure from nimble AI startups. Lemkin notes that as fast-moving AI tools deliver new capabilities daily, incumbents with legacy UIs and five-year roadmaps can no longer rest on brand strength alone. Growth-stage valuations are sliding back toward single digits of ARR, and what used to be a durable platform feels brittle. Founders must ask, “How can we integrate AI now—before newer entrants eat our lunch?” Whether it’s adding generative AI features inside a CRM or automating repetitive legal tasks, the choice is stark: innovate relentlessly or risk obsolescence. The rallying cry is simple: “Innovate or die.”

Inside the Office of OpenAI

OpenAI’s headquarters exemplify the fever pitch around AI innovation. With roughly 4,500 employees, the company surged to a 70-plus billion-dollar valuation in under two years. Yet even here, retention is a challenge—only about 60% of hires stay past two years, fueling a revolving door of talent. That dynamic creates both risk and opportunity: startups can snatch seasoned AI engineers eager for the next frontier. Meanwhile, protocols like Microsoft’s MCP (Microsoft Connected Platform) are helping products plug into enterprise apps without bespoke integrations. Behind the fast pace lies a simple fact: as AI interfaces become primary, legacy apps that force you to learn menus and tabs will wither away.

How to be an AI Billionaire

The path to wealth in AI may look daunting, but Lemkin offers a clear revenue benchmark: to justify a new hire, you need roughly $1 million in incremental revenue. If a startup can scale headcount without matching top-line growth, profitability vanishes. At the same time, seed-stage valuations have soared—many rounds now close at $60–100 million pre-money, with investors bracing for higher loss rates. Seventy percent of venture dollars today pour into late-stage “growth” rounds, chasing billion-dollar outcomes in AI infrastructure and apps. Yet at seed, it only takes one $10 billion exit to return an entire fund. Lemkin’s goal: snag at least one deal where he owns ~10% at seed and watch it scale into a generational business.

The Story of Saastr

After exiting his second startup in 2012, Lemkin launched Saastr by writing one blog post a day about mistakes he made building B2B software. No grand strategy—just a consistent cadence of honest lessons. Early on, he answered one Quora question daily to spark engagement. That content magnet led to three regional meetups and eventually Saastr Annual, which now generates over $25 million in revenue with just five employees—nearly $5 million per person. By openly sharing wins and failures, Saastr built a loyal community of SaaS founders who now trust its events and media. It’s a masterclass in content marketing: authenticity trumps polish, and consistency compounds faster than paid ads.

Being a Relentless Recruiter

Whether you’re scaling from zero or hiring your next VP, relentless recruiting is non-negotiable. Lemkin urges founders to interview at least 200 top candidates for every key role—no shortcuts. Top recruiters wake at dawn with two “must-talk” profiles in hand and fill calendars before lunch. They chase referrals, cold email founders who shine in webinars, and review GitHub projects until they discover hidden gems. The payoff: a team that delivers peak performance and retains that performance under pressure. As Lemkin quips, “You don’t just fill seats; you build a culture of excellence.”

Seeing Through the Fog of War

Navigating today’s AI landscape is like marching through a battlefield in dense fog. Yesterday’s dominators—large CPaaS providers, CRM giants—can be blindsided by new models or aggregator layers. Founders must ship “insanely good software” and then double down on dominating a niche market. That pattern held true in earlier eras—zero to one was rare, one to ten was tough, but ten to 100 often felt inevitable. AI has shattered that punch-card formula. Now every tier faces disruption, and competition shows up overnight. The key to clarity: stay laser-focused on a narrowly defined problem, iterate rapidly on user feedback, and guard against feature creep. True advantage will come to those who see five steps ahead, not just who can build the next chatbot.

The Future of Work for Gen Alpha

The next generation is rewriting the employment playbook. Lemkin observes that many teenagers he knows would rather live cheaply abroad and monetize online than pursue a traditional job. Nearly 10% of his son’s high school class opted out of college entirely, planning to build “digital nomad” careers in Eastern Europe or Southeast Asia. Meanwhile, Gen Z college students are already mapping tracks to graduate school as a way to defer full-time roles. What does this mean for founders? You’ll need flexible roles, project-based contracts, and AI-augmented workflows to attract young talent. Tasks like session summaries, basic customer support, or content editing can shift to well-trained AI agents. Human hires will excel in creative problem solving, relationship building, and cross-domain strategy—roles that AI can’t fully replicate.

Key Takeaways:

• Innovate or Die: Traditional software brands must integrate AI continuously or cede ground to startups.
• Leverage AI Doubles: Train a digital version of yourself with your content to handle 10× the volume and uncover candid user feedback.
• Recruit Relentlessly: Interview 200 candidates for crucial roles to secure top talent and build a high-performance culture.

What strategies will you adopt next to stay ahead in the dynamic world of AI?