In an era where ChatGPT can write marketing plans, and billion-dollar startups are snapped up before their founders can print business cards, navigating entrepreneurship has become more like a chess match than a sprint. Joseph Safina—investor, founder, dealmaker, and now author of Deal Mode—offers a grounded, clear-eyed perspective on how today’s entrepreneurs cannot just survive, but thrive, in the new age of AI and acquisitions.
Forget the hype. Safina isn’t here to sell you on a 10x mindset or crypto riches. He’s here to talk about building real businesses, making smart exits, and most importantly, thinking strategically in a world that’s moving faster than ever.
Why AI Isn’t Going to Replace You (Yet)
There’s a running joke in the startup world: “Will AI take your job, or just write better fundraising emails than you?” Either way, artificial intelligence is now embedded in nearly every part of running a business. From customer service bots to predictive sales analytics, tools powered by AI are giving founders superpowers—if they know how to use them.
Safina sees AI as an equalizer. “Entrepreneurs today can access tools that Fortune 500 companies couldn’t dream of ten years ago,” he says. But he’s quick to add a caveat: AI is a tool, not a substitute for judgment. “It can tell you what your customers are doing. It can’t tell you why they’re doing it. That’s still your job.”
Founders who rely too heavily on automation, he warns, risk losing touch with their own business intuition, the same instinct that often separates successful exits from flameouts.
Exit Strategy Starts on Day One
Safina’s biggest piece of advice? “If you think about your exit only when you’re tired, it’s already too late.”
In Deal Mode, Safina lays out a roadmap that begins not at the moment of sale, but at the company’s inception. He encourages founders to build companies with optionality—to develop products and structures that are attractive to acquirers, even if they don’t plan to sell anytime soon.
This means maintaining clean financials, documenting internal processes, building recurring revenue, and reducing dependency on any single client or employee. “Buyers don’t pay a premium for chaos,” Safina deadpans.
He also advises paying attention to market signals. In recent years, M&A activity has surged, particularly in sectors like fintech, AI, and healthtech. According to PwC, 2024 saw over $2.5 trillion in global M&A deals, a significant rebound driven by strategic consolidation and technological transformation. “Companies aren’t just buying revenue anymore,” Safina says. “They’re buying innovation. They’re buying people. They’re buying future relevance.”
The Soft Side of Hard Deals
Selling a business isn’t just financial—it’s emotional. Many founders define themselves by what they’ve built. So the idea of handing over the reins, even for a high price, can trigger anxiety, fear, or even guilt.
Safina doesn’t shy away from this. “Selling your company is one of the most personal professional decisions you’ll ever make,” he says. He encourages founders to think about their identity after the exit. What will drive them? What role do they want to play in the next chapter?
And just as importantly: What legacy are they leaving behind?
“Empowered entrepreneurship isn’t just about how you build,” he says. “It’s about how you leave.”
Smarter, Not Just Faster
Today’s startup ecosystem is obsessed with speed—scale fast, raise fast, exit fast. Safina suggests a different approach: clarity over haste. “Founders who know what they’re building and why tend to get better exits, even if it takes a little longer.”
He champions disciplined entrepreneurship: knowing your numbers, understanding your market, and having a game plan whether you raise a Series A or not. It’s the kind of practical wisdom that’s easy to overlook amid Twitter threads and pitch decks.
Final Thoughts
Joseph Safina’s vision isn’t about disrupting the system, it’s about mastering it. In the age of AI and acquisitions, real power lies not in having the flashiest tech or the highest valuation, but in making thoughtful, strategic decisions from day one.
So yes, maybe AI will write better cold emails. And yes, maybe your startup will get acquired by a company that didn’t exist three years ago. But if you’re playing the long game—with your eyes open, your books clean, and your purpose intact—you’ll be ready.
And as Safina might say: “That’s when you’re in deal mode.”
