Lessons in Rejection: How Andy Trattner Turned “No” Into His Best Strategy

Andy Trattner didn’t always picture himself leading a startup. As a kid growing up in Wisconsin, he was more focused on video games, chess, and building Lego contraptions than charting out a future. But somewhere between a childhood marked by personal upheaval and a career path defined by uncertainty, Trattner developed a mindset that now fuels his role as co-founder and COO of Shuffle, a modern take on speed dating that blends human connection with tech-savvy design.

“The only time I ever thought about a career as a kid,” Trattner recalls, “was when I saw a James Bond movie and asked my dad how to become the guy who builds all the gadgets.”

From there, the journey wasn’t a straight line. Not even close.

Getting Comfortable with Getting Lost

After graduating from MIT, Trattner didn’t jump straight into a polished tech role or executive training program. Instead, he drove for Uber, tutored kids, wrote a daily blog, and wandered through various job attempts until he found his footing. He crashed on couches. He got fired. He quit jobs he hated. And somehow, he kept moving forward.

“I really wanted to start a company, but I had no idea how. I ran out of patience with myself,” he says. “It was painful and slow, not having mentors I could talk to. But that’s how I started figuring things out.”

Eventually, he joined Scale AI, initially as a customer support hire, where he quickly earned more responsibility through grit and results. Within nine months, he was managing high-stakes accounts and overseeing data pipelines for training self-driving cars. Still, when it became clear he wasn’t being compensated fairly for the value he brought, Trattner walked away.

“I’ve always known I wanted to build something of my own. So if a job wasn’t aligned with that or didn’t give me the room to grow, I left.”

Understanding the Market (and Yourself)

After leaving Scale AI, Trattner moved to Ecuador. The experience was formative, not just personally, but professionally. It’s where he launched Senseg, a fintech experiment that ultimately didn’t last, but it gave him what he now considers the foundation of any successful business: a deep understanding of the market. 

“You can learn tactics. You can learn how to code, write emails, whatever,” he says. “But if you don’t understand the conditions of the world, you can’t change them. Most people don’t deeply understand markets, and that’s why their ideas don’t land.”

For Trattner, Ecuador turned theory into action. He and his team helped pass legislation, a moment that reshaped his view of personal and professional agency. “It was a small enough economy where you could actually move the needle. That’s where I learned what real agency felt like.”

The Role of Feedback, Failure, and High Agency

Building a dating serviceapp like Shuffle, with a strong real-world social element, guarantees one thing: feedback. Sometimes it’s helpful, sometimes it stings. For Trattner, that’s exactly the point. 

“You need a lot of feedback to understand what matters,” he says. “You can’t be afraid of what people think, but you also can’t ignore it. You have to recognize what’s meaningful without letting it crush you.”

Trattner applies this same attitude to failure. For him, it’s not a setback, it’s a recalibration.

“When things don’t work out, I move fast. Tomorrow, try something new. That’s my whole model,” he explains. “You don’t just get the right answer on the first try. You get there by trying again.” 

Redefining Success: The Power Law Mindset

Trattner’s relationship with success has evolved over time. He doesn’t believe in one-size-fits-all wins. Instead, he sees success as a series of experiments. The real trick is volume.

“Most people don’t tell you this,” he says, “but you need to try 20 jobs to find one that fits. Same with friendships. Same with startups. You make 20 bets and keep the one that works.”

This is what he calls the power law mindset, the idea that a single breakthrough can deliver more impact than a string of small successes. But to unlock that one breakthrough, you have to be willing to take the risk, put in the effort, and accept a whole lot of rejection along the way. You have to aim for the iPhone and not settle for building the Blackberry, Palm Pilot, or the Razr.  

Takeaways for Professionals Navigating Change

Trattner’s career offers more than just an inspiring founder story. It’s a playbook for anyone navigating career pivots, uncertainty, or burnout. Here are a few takeaways that stood out from our conversation.

1. Write it Out: Getting your thoughts down can help organize what feels overwhelming. A regular writing habit—journaling, note-taking, or blogging—can bring clarity and highlight patterns. 
2. Understand Your Market: Whether you’re applying for jobs, launching a business, or pitching a new idea, know the landscape you’re entering. Read deeply. Ask questions. Get feedback.
3. Be Okay With Failure, But Move Fast: Rejection isn’t the end of the story. It’s part of building the right one. “Tomorrow, try something new,” Trattner says. That mindset matters.
4. Make More Bets: Whether it’s experimenting with career moves, networking, or business ideas, volume matters. Not every attempt will land, but one just might change everything.

Charting the Path Forward

Andy Trattner didn’t have a roadmap. He made one by trial, error, and relentless curiosity. His career is a reminder that uncertainty isn’t something to avoid. It’s something to move through, one smart risk at a time.