Entrepreneurship is far from a clean, straight path. If you’ve ever tried building something from scratch, you know exactly what I’m talking about. It’s messy. Plans fall apart, unexpected hurdles pop up, and sometimes, the whole thing feels like it’s one step away from a total disaster. That’s exactly what I got from my conversation with Jonathan Brambles, better known as The Email Guy. He’s been through his fair share of chaos, and what stood out to me most was how he leaned into it instead of running from it. Jonathan didn’t set out to be an email marketer, but he figured it out along the way. And in the mess, he found a way to not just survive, but thrive.
Jonathan’s story made me realize that entrepreneurship is all about embracing uncertainty, even when it feels like you’re in over your head. His career journey, from building houses to sending millions of emails a day, is packed with lessons for anyone who’s ever felt lost or unsure about what’s next.
Stop Aiming for Perfection—Get Messy Instead
Jonathan’s journey into email marketing wasn’t planned, and that’s probably one of the biggest takeaways. He didn’t wake up one day and decide, “I’m going to master email.” Like many of us, he stumbled into it, adapted, and eventually made it his thing. His career started in Silicon Valley during the boom of startups, and he quickly saw how messy things could get. But instead of running from the chaos, Jonathan embraced it. He told me about a time when he was working at a startup that completely tanked right after he was hired. “They brought me in, told me they’d give me the sun, moon, and stars, and a week later, they crashed. Welcome to Silicon Valley.”
He didn’t let the failure scare him off. Instead, he learned from it and took those lessons into his next ventures. Jonathan realized that waiting for the perfect opportunity or the “right” moment to make a move in business is just another form of procrastination. You have to dive in and get your hands dirty. There’s never a perfect time, and honestly, the mess is where all the real learning happens.
Key Takeaways from Our Discussion:
- Perfection isn’t the goal: Stop waiting for everything to line up perfectly. Just dive in and learn as you go.
- Every failure is a lesson: Jonathan didn’t view his early setbacks as defeats. Instead, he used them to get better.
- The mess is where the magic happens: The sooner you stop fighting the chaos and start embracing it, the quicker you’ll find your stride.
It’s All About Building Real Relationships
One thing that really stuck with me from Jonathan’s story is how he prioritizes relationships over transactions. His business isn’t about squeezing every last dollar out of a client; it’s about creating genuine, lasting connections. There was this one time he was preparing to launch a huge campaign, and right before they were set to go live, a hurricane hit the area they were targeting. They had every reason to push forward with the campaign anyway, but instead, Jonathan’s team took a step back. “We paused and thought, ‘How can we actually help these people right now?’” They pivoted their approach, focusing on offering real support to the affected families rather than pushing products. The result? They not only met their goals—they had their best month in sales ever.
His approach to business was simple: be human. People can tell when you’re just trying to sell them something. But when you actually care about helping them, they’ll stick with you for the long haul. It’s something I’ve seen time and time again in my own journey, too. You don’t have to be a shark to succeed. In fact, being genuine and building trust will get you a lot further.
What I Learned from His Experience:
- Relationships over transactions: Don’t focus solely on the sale. Focus on the person.
- Pivot when necessary: Sometimes, the best thing you can do is change course. It’s not a sign of weakness—it’s smart business.
- People appreciate authenticity: Jonathan’s success came from being real with his customers, and that’s a lesson worth remembering.
Reflections from the Interview
Talking with Jonathan made me reflect on my own experiences as an entrepreneur. We’ve all had those moments where things didn’t go as planned—sometimes it feels like nothing goes as planned—but his story reminded me that it’s okay to not have everything figured out. His success didn’t come from being perfect or following a strict path. It came from being adaptable, honest, and willing to roll with the punches. And at the end of the day, that’s what entrepreneurship is all about: learning, adapting, and pushing forward, even when things get messy.
Here’s What I’m Taking Away:
- Perfection is overrated: Aiming for 99% is better than holding out for 100% and never getting started.
- Authenticity wins: People respond to honesty and realness, not slick sales tactics.
- Trust your gut: Sometimes, the best business decision is the one that feels right, even if it doesn’t follow conventional wisdom.
- Failure is part of the process: Every entrepreneur has failed at something. What matters is how you bounce back.
- Stay flexible: The ability to pivot and adapt is one of the most important skills an entrepreneur can have.
Final Thoughts
Jonathan’s story isn’t just about email marketing or startups. It’s about learning to navigate the messiness of entrepreneurship and finding success in the middle of it. If there’s one thing I took away from our conversation, it’s that you don’t have to have all the answers to get started. In fact, waiting until you have everything figured out is probably the worst thing you can do. Dive in, embrace the chaos, and trust that you’ll figure it out as you go.
Hear more from Jonathan Brambles and get the full scoop on his journey! Check out the full episode of the Never Been Promoted podcast: Cold Emailing vs. Warm Emailing: Which Works Better? | Jonathan Brambles
CONNECT WITH JONATHAN BRAMBLES:
LinkedIn: https://www.linkedin.com/in/jonathanbrambles/
Website: https://theemailguy.org/