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Surviving the Side Hustle
Welcome to "Surviving the Side Hustle," the ultimate podcast for balancing the demands of entrepreneurship with maintaining mental, physical, and emotional well-being.
Hosted by Coach Rob Tracz, an expert in helping driven professionals achieve 'personal development for professional success,' this show is more than just storytelling—it's a masterclass in thriving amidst the entrepreneurial grind. Each episode features candid conversations with leaders who are rewriting the rules of entrepreneurship, sharing their unique stories, the creative solutions they're offering, and the everyday challenges they’re overcoming.
Whether you’re a side hustler looking for your big break or an established entrepreneur seeking fresh perspectives, "Surviving the Side Hustle" provides valuable insights that resonate with the movers, the shakers, and everyone in between.
Feeling burnt out and sidelining your own health? This podcast empowers you to overcome stagnation, build resilience, and optimize your life and business. We dive deep into your goals, identify obstacles, and share strategies to boost your energy, improve your strength, and keep the entrepreneurial grind enjoyable.
Join us for inspiring stories, expert insights, and practical advice to help you look good, feel good, and do great things at every stage of your entrepreneurial journey. Let’s not just survive the side hustle—let's master it.
Surviving the Side Hustle
E108 - Jordan Calderon Recap: Lessons From College Hustle to Building Sellable Businesses
Ever wonder why some entrepreneurs can walk away from their businesses with millions while others remain chained to theirs forever? This revealing conversation with Jordan Calderon, two-time exited founder and president of top 100 marketing agency StratDev, challenges everything you think you know about building a sustainable business.
Jordan drops a truth bomb that most entrepreneurs never consider: build your business like you plan to sell it, even if that's not your goal. Clean systems, founder independence, and clear transition plans aren't just exit strategies—they're the foundation of a healthy operation. As Rob reflects, this buyer's mindset fundamentally changes how you approach growth, prompting a crucial question: if someone took over your business tomorrow, would they find clear procedures or chaotic confusion?
The conversation takes a fascinating turn when Jordan shares how, at 20, he pitched clients twice his age while looking 16. After initially trying to fake maturity, he made a breakthrough by embracing his youth as his superpower. "I know how to market to young people better than you do" became his winning differentiator. This authentic approach exemplifies Rob's coaching principle: stop wasting energy pretending to be someone else—real credibility comes from owning your unique perspective.
Perhaps most impressive is StratDev's remarkable achievement of almost zero turnover in five years. Jordan's secret? Small, consistent signals of care—from gift cards and hotel giveaways to a dedicated Slack channel celebrating wins. Most surprising is his daily 30-minute block specifically for showing appreciation to his girlfriend and team members. This intentional culture-building demonstrates that high-performing businesses are built on high-trust relationships cultivated through genuine care.
Ready to transform your approach? As Jordan says: "Just do it, take action, jump off the cliff and figure out how to fly on the way down." Schedule a strategy session at survivingthesidehustle.com/freecall to build sellable systems, develop leadership habits, and create a business that grows while building a life that fulfills.
What's going on? Everybody Rob here, and welcome again to another Friday recap episode of Surviving the Side Hustle. This week, I sat down with Jordan Calderon, a two-time exited founder and president of StratDev, which is a top 100 marketing agency. We talked about how to build a sellable business, create a team culture people never want to leave and the importance of blocking time for love, literally. And today I'm here to walk you through my big three takeaways, plus how they connect to the exact frameworks I use my coaching clients to help them grow with purpose.
Speaker 1:So Jordan dropped the bomb that most entrepreneurs never really think about. He said how you can't wait until you want to sell your business. Instead, you want to build a sellable business from day one. He talked about the importance of clean systems, founder independence and a clear transition plan, but what hit me most was his mindset. He thinks like a buyer even when he's still building. This ties directly to my principle all about opportunity, specifically about the importance on how important it is to keep showing up. Jordan shows up not just to grow, but to future-proof. So here's a coaching question for you If someone took over your life or your business tomorrow, would they have clear procedures to follow or would they be stuck in your chaos?
Speaker 1:Jordan shared how, at 20 years old, he was pitching clients twice his age and getting dismissed because he looked like he was 16. His first instinct was to fake it, act older and be someone he's not, but eventually he embraced it and said you know what? I am young, but I know how to market to other young people better than you do, and that is some resilience. Specifically, he figured out how to identify the right challenge. So instead of fighting his youth, he reframed it as a strategic advantage. So the coaching takeaway here is stop trying to be someone else to gain credibility. Real growth comes when you own your own lane and let the results speak for themselves. Jordan also talked about how his company, stratdev, has had almost zero turnover in five years. That's unheard of His secret. Small signals of care like visa gift cards on birthdays, hotel giveaways for team members who've been really grinding an accolades Slack channel to celebrate wins, and my favorite is time blocking 30 minutes every day to show his girlfriend love and appreciation and other team members that need to be touched with. And to me, that's culture. He's creating culture from his leadership and to tie it back to prime performance. That's all about principle number five, where we dive in on social support and influence, specifically talking about the team triangle again. And Jordan doesn't have just any team, he's building a team of leaders.
Speaker 1:So who do you need to acknowledge today? Who's helping you behind the scenes emotionally, mentally or logistically that you've been overlooking? High performing businesses start with high trust relationships, so remember that. And, to recap, you want to start building your business like you're planning to sell it, even if you never really want to Own what makes you different. Don't waste energy faking someone else's path and lead your team and your life with simple acts of consistent care. That's how you create a business that grows and a life that fulfills you. And if you want help building your sellable systems, leadership habits or brand strategy, head over to survivingthesidehustlecom forward slash free call and let's hop ona strategy session and chat about it. We'll go over lots of things like different tools that you can use in your business or in your personal life to help you through burnout, overcome stagnation and scale your personal life and growth.
Speaker 1:And if you haven't listened to the full episode with Jordan yet, go back and check it out. It's literally a masterclass, powerful stuff, and I'll leave you with something powerful that Jordan said at the end. That's really been stuck in my head all week. He said just do it, take action, jump off the cliff and figure out how to fly on the way down. That's really what this show is all about, and I appreciate you guys showing up and listening and I'll see you guys next time. Peace, peace, peace.