The Long Game: Why the Best Prospectors Measure Success in Years
By: Eric JanssenStop Asking to Pick My Brain: What a Top Sports Agent Wishes Sellers Knew
Shari Wenk built a half-billion-dollar career one follow-up at a time. Here's what she knows about prospecting that most sellers never learn.
When I reached out to legendary trainer Tim Grover (the man who trained Michael Jordan, Kobe Bryant, and Dwyane Wade) I wanted to understand what separates the unstoppable from everyone else. Grover was interested, but he didn't hesitate with his response.
"Talk to Shari," he said, pointing me toward his longtime business partner and co-author.
Shari Wenk has negotiated nearly half a billion dollars in deals. She's represented icons like Terry Bradshaw, Sam Smith, Dennis Rodman, and the Tiger Woods Foundation. She co-authored Relentless and Winning—books that have sold over a million copies and reshaped how athletes and entrepreneurs think about performance.
But here's what makes her story remarkable: she wasn't born into connections. She built her career from scratch, one outreach at a time, in an industry that didn't yet exist when she started.
In an age of AI-driven messaging and cookie-cutter sales automation, Wenk's approach feels almost anachronistic. She's relentlessly persistent, but in a way that's grounded in genuine relationship building. Her career proves something most modern sales methodologies ignore: the relationships that matter most are built over years, not quarters.
Here are eight lessons from Wenk that challenge conventional prospecting wisdom, and offer a roadmap for building a career that lasts.
1. The 18-Year Follow-Up
Wenk's partnership with Tim Grover didn't happen overnight. It took 18 years.
Early in their careers, they worked together on a book deal that fell through. Most agents would have moved on. Wenk didn't. She stayed in touch—not with pressure or constant asks, but with simple, genuine gestures. Congratulations on a new achievement. A quick note after an event. Thoughtful, consistent touches over nearly two decades.
When Grover was finally ready with an idea for a book, Wenk was the first person he called.
Her response? "I knew you'd eventually come back."
That persistence led to Relentless—a book that has sold more than a million copies and fundamentally changed how people think about elite performance.
This story encapsulates everything that's wrong with modern prospecting metrics. Most sales organizations measure success in 30-day cycles. Pipeline velocity. Quarter-over-quarter growth. Monthly quota attainment. None of those metrics would capture the value of an 18-year relationship.
Yet the person who says no today may transform your career years down the line. The question is: are you building a system that allows for that possibility?
2. Reframe Rejection as Part of the Process
Most people treat rejection as failure. Wenk treats it as the job itself.
"The sooner you can accept that rejection is part of your business, you don't take it so personally," she explains.
Sales isn't a profession where every call ends in yes. It's a profession where no is the most common answer you'll ever hear. The difference between successful sellers and everyone else isn't that they avoid rejection—it's that they've stopped interpreting rejection as a referendum on their worth.
Wenk reframes rejection as proof that you're working the process. If you're hearing no, it means you're putting yourself out there and creating opportunities. The goal isn't to avoid rejection. The goal is to outlast it.
This mindset shift is critical because it prevents the emotional spiral that derails most prospecting efforts. When rejection becomes personal, you hesitate before the next call. You second-guess your approach. You start softening your message to avoid hearing no. All of which makes you less effective.
Stay in the game long enough, and the right yes will eventually surface.
3. Silence Doesn't Mean No
A lack of response can feel crushing. But Wenk doesn't interpret silence as rejection.
"Silence can just be silence," she says.
That prospect who hasn't replied to your LinkedIn message isn't sitting around plotting how to ignore you. They're buried in emails, juggling meetings, trying to make it through the week. Your outreach simply didn't rise above the noise.
The answer isn't to give up. It's to follow up—gently, persistently.
"Bump it again," Wenk advises. "It's not personal rejection. You just didn't ring their bell on the first one."
The key word: gently. Not daily. Not annoyingly. But enough to demonstrate that you're still there and still relevant. And critically, don't just follow up to follow up. Each touch should add value.
"I think those first inquiries have to have something in them that makes people see that you understand—that you're there to solve a problem they may be having," Wenk explains.
Silence is neutral. It doesn't mean rejection until someone explicitly says no. Most sellers give up too early, mistaking silence for disinterest when it's really just noise.
4. Master the Market, Not Just the Pitch
When Wenk broke into sports marketing and publishing, she didn't obsess over perfecting her pitch or memorizing scripts. She became obsessed with the product.
"I wasn't so much focused on learning how to do my craft. I was focused—I was obsessed—with learning what I was selling," she says. "The product, in my case, would have been an athlete, a book concept... 'why the world needs this book.'"
She devoured every issue of Sports Illustrated. Every week. Cover to cover.
"I read every single word of every magazine, every week," she recalls. "I didn't have to be the expert—I just had to find the experts who could write the books, and I could manage and publish them."
That deep market understanding made her invaluable. She became known as the person who could get sports books done—long before "sports marketing" was even a defined industry category.
This principle applies everywhere. Decision-makers can immediately tell when you've done your homework. They want to know you understand their world, not just your product. Sales tactics alone won't earn trust. But mastery of the market? That makes you unforgettable.
5. Never Ask to "Pick Someone's Brain"
If you've ever asked a busy executive for 15 minutes to "pick their brain," Wenk has a blunt response.
"You cannot. My brain is not to be picked. If you can pick my brain in 15 minutes, I don't have much of a brain."
The problem with brain-picking requests is that they're entirely extractive. They ask for time without offering value in return.
Wenk's advice: flip the script. Deliver value first.
That could mean sharing a relevant insight, sending something genuinely useful, or demonstrating that you've thought deeply about their world. Once you've done that—once you've proven you're not just another person asking for favors—then you can request time to discuss next steps.
That simple shift changes everything. You stop being noise and start being signal.
6. Keep Your Mind Stronger Than Your Feelings
Sales is emotional work. There's excitement when you think you've got a win, frustration when someone pushes back, and fear when a deal is on the line.
Wenk's rule: don't let those emotions take over.
"Your mind has to be stronger than your feelings in business," she says.
In practice, that means staying calm under pressure. When a prospect challenges your pitch or questions your value, they're not attacking you personally. They're doing business. If they're skeptical, it's part of the process, not a personal affront.
"Staying calm is everything," Wenk explains. "As soon as you get emotional, they're in your head. Now you're thinking about the wrong thing—you've lost focus on your purpose for the meeting."
The person who stays calm and clear-headed maintains control of the conversation. Emotional discipline isn't innate—it's a skill you can develop through deliberate practice. But it's one of the most valuable tools you can master in prospecting and negotiation.
7. Negotiate as Collaboration, Not Combat
Too many people approach negotiation like warfare—as if there must be a winner and a loser.
Wenk rejects that mindset entirely.
"To me, a good negotiation is a collaboration," she says.
It's about building something that works for both sides. The question isn't "How do I win?" but "How do we both get what we need?"
In practice, Wenk turns potential obstacles into shared problems. Instead of waiting for a prospect to surface an issue, she's proactive:
"This is gonna be an issue. How can we bridge that?"
"I make it a 'we problem' so that we both need to solve this," she explains, "because we probably both want this deal to work, right? If we've come to negotiation, we both have an interest in the end result."
That simple reframe can completely change the dynamic of a meeting. It removes tension and replaces it with partnership. The other side stops bracing for a fight and starts working with you to find solutions.
8. Know Your Price and Say It Without Apologizing
When it comes to pricing, Wenk doesn't hesitate.
"Your doctor knows what his fee is. Your lawyer knows what their fee is. Everything has a price. Why don't you know your price?"
Too many professionals apologize for their rates. They offer ranges. They discount before they're even asked. Wenk rejects all of that.
Her rule is clear: "We have a fee. We don't hedge the fee."
Knowing your price is about more than numbers. It's about confidence. It signals that you believe in the value of your work. And it teaches clients to respect it.
When you hedge on price, you're telling the prospect that your value is negotiable. When you state it clearly and confidently, you're communicating that you're worth what you're asking.
Built to Last
Shari Wenk's career proves that success doesn't come from shortcuts or magic scripts. It comes from persistence, clarity, and professionalism—repeated day after day, week after week, year after year.
She didn't become a top agent because of one viral pitch. She became one because she kept showing up. She studied her market, stayed in touch, and played the long game.
The results speak for themselves: nearly half a billion dollars in deals, multiple New York Times bestsellers, and partnerships with legends across sports and business.
In a world addicted to instant results, her approach feels almost radical. But the lesson is clear: don't rush the process. Build the habits. Do the homework. Make the calls. Follow up. Stay calm. Hold your price.
If you do those things consistently—if you're willing to measure success in years instead of quarters—you won't just close deals. You'll build a career that lasts.
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Eric Janssen teaches sales and entrepreneurship at the Ivey Business School at Western University. He is the founder of the Founder Sales Sprint and host of the Sales Reframed podcast, where he interviews Shari Wenk in Episode 3.
He is the founder of the Founder Sales Sprint and host of the Sales Reframed podcast, where he interviews Shari Wenk in Episode 3.
