Running Two Startups Without Losing Your Mind (or Your Family Time) with Brian Lee
Running Two Startups Without Losing Your Mind (or Your Family Time) – with Brian Lee
Running two startups without burnout is possible by focusing on systems, delegation, and intentional time use, allowing founders to scale businesses, protect family time, and work smarter daily.
In today’s hustle-happy world, it’s easy to believe that success requires 80-hour workweeks, endless to-do lists, and constant stress. But what if you could grow two thriving businesses and raise a toddler — without burning out?
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That’s exactly what Brian Lee, founder of Roamly and Gildre, is doing. In this powerful episode of the Lazy Entrepreneur Podcast, Brian opens up about building scalable startups, balancing family life, and working smarter with the help of systems, delegation, and AI.
From Corporate to Creative: Brian’s Founder Journey
Brian didn’t start out as a startup guy. He spent the first decade of his career in corporate CPG before diving into entrepreneurship by launching escape rooms across the U.S. That experience led him to co-found Roamly, a travel tech platform helping people discover authentic, local experiences in cities across the globe.
When the pandemic disrupted the travel industry, Brian pivoted — not away from entrepreneurship, but toward something deeper. He co-founded Gilder, a private founder community focused on authentic support, two-way learning, and building what he calls “your personal founder advisory board.”
Balancing Two Startups and a Baby
Running one startup is hard. Running two — with a 15-month-old daughter at home — sounds nearly impossible. But Brian’s figured out how to do it without losing his mind:
He segments his days and weeks to focus on one company at a time, instead of task-switching endlessly.
He delegates tasks that drain his energy or don’t require his unique skillset.
He relies on smart systems and community, especially when his time is stretched thin.
His biggest realization? You don’t have to do it all to move the needle. You just need to focus on what matters most.
The Lazy Entrepreneur Mindset
Brian doesn’t believe in glorifying hustle. Like many of us, he used to feel guilty for working “too little” or “too much,” constantly comparing his schedule to other founders. But over time, he realized that intentionality beats hours worked — every time.
Here’s how he works smarter:
AI tools like ChatGPT and Gemini help him research, brainstorm, and automate repetitive tasks.
He avoids unnecessary internal meetings and protects his time for deep work.
He focuses on impact, not effort — prioritizing tasks that move the business forward, not just keep him busy.
As he says, “Just cranking out work for 100 hours a week isn’t the answer. Being effective is.”
His Lazy Entrepreneur Tip?
Segment your time based on energy levels. Identify your A-level, B-level, and C-level hours, and schedule your most important tasks accordingly. Then delegate or defer what doesn’t truly matter.
“The goal isn’t to work less just for the sake of it — it’s to be more intentional with your time so you can build a business and a life you love.”
Final Thoughts
Brian is living proof that ambition and peace of mind can co-exist. By building with purpose, leveraging AI and systems, and refusing to wear “busy” as a badge of honor, he’s created not one — but two — companies that support both his entrepreneurial dreams and his family life.
Want more tips on building a business without burning out?
Subscribe to the Lazy Entrepreneur Podcast and follow Kristy Yoder for weekly episodes that help you delegate, automate, and dominate — without the hustle.
Learn more about Brian Lee:
https://www.linkedin.com/in/brianconnorlee-gildre/
Protect Your Time While Growing Your Revenue
If you’re an overwhelmed entrepreneur who wants sustainable business growth, stronger systems, and real freedom, I offer business coaching and mentorship designed for founders who want to scale without burning out.
This is for the lazy entrepreneur who values clarity, structure, and long-term profitability.
👉 BOOK A FREE CONSULTATION HERE.
Build your business strong before you step away.
Frequently Asked Questions
Is it possible to run two startups without burning out?
Yes. Running multiple startups sustainably requires clear priorities, strong systems, effective delegation, and disciplined time management. Founders who focus on impact instead of hours worked can scale without sacrificing their health or family life.
How do founders balance entrepreneurship and family life?
Successful founders intentionally segment their schedules, protect family time, and eliminate unnecessary work. They prioritize deep work, delegate lower-value tasks, and build support systems both at home and in their business.
What is the “Lazy Entrepreneur” mindset?
The Lazy Entrepreneur mindset focuses on efficiency over hustle. Instead of glorifying long hours, it emphasizes working smarter through automation, delegation, and strategic decision-making to maximize results with less stress.
How can AI help startup founders save time?
AI tools can assist with research, brainstorming, content creation, customer support drafts, and task automation. By offloading repetitive cognitive work, founders free up time for strategic thinking and high-impact decisions.
