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From Trailer Park to Tech Founder
How Jeremy turned personal challenges into TaskMagic, a $1.8M automation solution.
Welcome to Money Making Story,

Today, we’re thrilled to share the story of Jeremy Redman, who rose from a trailer park to build TaskMagic, a $1.8 million automation app.
In this discussion, we’ll discuss his:
Top Advice from Jeremy
The Struggle Before Success
Discovering the Power of Automation
Bootstrapping the Dream
Must have Essential Skills!
Lessons in Resilience
Building Community and Brand
Lessons for Aspiring Entrepreneurs
“You Can Do It Too”
A Story Worth Reading
Top Advice from Jeremy:
“Keep it simple, take consistent action, and solve real problems for your customers.”
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Jeremy Redman’s journey is a quintessential rags-to-riches story, filled with grit, innovation, and a relentless drive to succeed. From growing up in a trailer park to creating TaskMagic, a million-dollar app that automates workflows using no-code and AI, Jeremy’s story is both inspiring and instructive for aspiring entrepreneurs.
Here’s how Jeremy transformed his setbacks into a stepping stone for massive success, and how his strategies can help others do the same.
The Struggle Before Success
Jeremy’s early life was anything but easy. Raised by a single mom who worked tirelessly to make ends meet, Jeremy had a rough start. He struggled with self-doubt and faced repeated failures, getting fired from nearly every job he held.
“I grew up in a trailer park. My dad left when I was eight or nine. My mom worked two jobs. There’s no way people get out of what I was in,” Jeremy recalls.
Despite the odds, Jeremy always searched for a way to break out of his circumstances. He credits his persistence and willingness to try new things for helping him rise above his humble beginnings.
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Discovering the Power of Automation
Jeremy's obsession with efficiency began during his first startup job. While there, he restructured a pay system for thousands of contractors in his first week. The experience left him addicted to creating change at scale.
This obsession later led him to create TaskMagic. The idea was born when customers sent videos asking for help with automation workflows. Jeremy thought, “What if we could turn their video into the automation itself?” This simple yet revolutionary idea was the foundation for TaskMagic.
Bootstrapping the Dream
Starting TaskMagic wasn’t smooth sailing. Jeremy didn’t have a trust fund or investors backing him. Instead, he relied on scrappy, unconventional marketing strategies and hard work.
Here are some tactics that worked for him:
Cold Outreach
Jeremy believes in the power of personalized outreach. He personally sent thousands of emails, DMs, and Loom videos to potential customers. His relentless cold-calling and personalized follow-ups converted a significant number of prospects into paying customers.“People want shortcuts, but the truth is you have to talk to people. Cold outreach costs your time, not money,” Jeremy says.
Strategic Partnerships and Acquisitions
Jeremy didn’t just build; he bought. By acquiring small companies and newsletters with aligned audiences, like a no-code newsletter with 11,000 subscribers, he expanded his reach and integrated their user bases into his ecosystem.AppSumo Launch
Leveraging AppSumo, a platform for distributing digital products, TaskMagic generated $1.8 million in just 100 days. Jeremy had modest expectations, but the campaign exceeded his wildest dreams.“I thought we’d hit $30k, maybe $100k. We did $1.8 million,” Jeremy recalls.
Lessons in Resilience
Jeremy emphasizes that success doesn’t come from fancy ad strategies or raising millions of dollars. Instead, it’s about:
Bias Toward Action: Stop overthinking and start doing. Jeremy’s advice is simple: “Go do something. Go make the wrong decision. The data will guide you.”
Personalized Customer Engagement: Jeremy personally answered over 1,500 customer questions. He believes founders must engage directly with users to understand their needs.
Handling Rejection: Cold outreach inevitably brings rejection, but Jeremy embraced it as part of the process. “Out of 300 emails, three will say yes. That’s how you win.”
Building Community and Brand
Beyond selling a product, Jeremy focused on creating a recognizable, trustworthy brand. He wanted TaskMagic to be more than an app—it had to be something people would proudly talk about.
His community-building efforts, including forums and YouTube content, have helped solidify TaskMagic as a trusted name in no-code automation.
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Lessons for Aspiring Entrepreneurs
Jeremy’s story offers actionable advice for anyone building a business:
Start Simple: You don’t need a revolutionary idea to start. Solve one problem well and grow from there.
Leverage Free Tools: Use cold outreach, forums, and other low-cost methods to connect with customers.
Be Scrappy: Don’t be afraid to test unconventional marketing methods, like Craigslist ads or micro-acquisitions.
Consistency Is Key: Whether it’s outreach, content creation, or customer engagement, consistency wins.
“You Can Do It Too”
Jeremy’s final message is clear: “You are valuable. You can do it. Everyone has something to give—figure out what that is and run with it.”
Whether you’re starting from scratch or trying to scale your business, Jeremy’s journey is a testament that with grit, creativity, and a relentless focus on customer needs, success is achievable—even for the underdog.
A Story Worth Reading
10 days after Trump's historic landslide:
Peter Thiel sat down with @bariweiss for his first post-election interview.
The Silicon Valley legend revealed what really happened behind the scenes.
And why 2024 wasn't just an election - it was a revolution:🧵
— Ben Averbook (@benaverbook)
1:42 PM • Nov 17, 2024
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