What if the smartest move for your business was not grinding harder, but designing a life where you can actually take a month off? Jake Brown and Caleb Bogia-Curles kick off Season 2 with a candid conversation about building a business that funds freedom now—not just someday—while sharing hilarious travel mishaps, ADHD-friendly family travel strategies, and practical ways to protect your time, energy, and wealth.

In this episode:

Caleb and Jake talk about:

1. Building a business that lets you take meaningful time off
   Jake and Caleb discuss treating business wealth as a way to fund the life you want now—not just a distant retirement.
2. Why rest can make your work—and ideas—better
   They explore how stepping away from the grind can refresh your perspective, renew your energy, and create space for better breakthroughs.
3. Practical travel strategies for ADHD families
   They share tips for managing time, money, food, hydration, sleep, exercise, and energy while traveling with a large family.

A line that stuck with us:

“A real break doesn’t take you away from your business—it helps you come back to it with fresh eyes.”

Resources & links mentioned:

• Ready to do some foundational work for your business? Setup a time to talk with Caleb here: https://calendly.com/caleb-focusedfounderswealthplanning/exploratory-call
• https://www.focusedfounderswealthplanning.com/process
• https://airballoonadvisory.com/
• https://airballoonadvisory.com/brainfrictionscore/

Connect with us:

Jake Brown is a fractional revenue executive and business coach who works with business owners and founders on marketing, sales, and growth. He has ADHD. He runs a business. He's figured out a lot of this the hard way — and talks about it openly.

• Jake on LinkedIn: linkedin.com/in/airballoon

Caleb Bogia-Curles is a Certified Financial Planner who works with ADHD entrepreneurs. He has ADHD. He runs a business. He built his entire practice around the gap between standard financial advice and the way ADHD brains actually work.

• Caleb on LinkedIn: https://www.linkedin.com/in/%F0%9F%93%88caleb-bogia-curles-cfp%C2%AE-964823b8/

About the show:

Doing Business with ADHD is for the late-diagnosed, the self-diagnosed, and the "I've always been this way but nobody ever called it anything" crowd — business owners and founders who are finally starting to understand why the standard playbook never quite worked for them.

Hosts Jake Brown and Caleb Bogia-Curles both have ADHD and both run businesses. Their conversations are honest, a little rambly, occasionally chase a squirrel or two — and somehow still land on real, practical advice about getting clients, getting paid, managing money, and building something sustainable.

The rules weren't written for your brain. Let's change the rules.

Travel can be overwhelming, especially for neurodivergent individuals. In this episode, Jake Brown shares his personalized travel system that minimizes decisions, reduces stress, and maximizes enjoyment, making travel more accessible and enjoyable for everyone. This episode offers applicable, step-by-step systems that anyone who struggles with decision fatigue or travel overwhelm can adapt. By externalizing decisions, creating routines, and choosing supports, you can transform travel from a stressor into an enjoyable experience.

Main Topics:

• Strategies for simplifying travel booking and avoiding decision fatigue
• His system for packing, packing duplicates, and preparing for travel days
• How externalizing decisions and routines help preserve executive function
• Tips for navigating airports efficiently with tools like Clear Plus
• Practical ways to make travel routines sustainable and enjoyable
• Insights into how mindset shifts improve travel experiences

Doing Business with ADHD is for the late-diagnosed, the self-diagnosed, and the "I've always been this way but nobody ever called it anything" crowd — business owners and founders who are finally starting to understand why the standard playbook never quite worked for them.

Hosts Jake Brown and Caleb Bogia-Curles both have ADHD and both run businesses. Their conversations are honest, a little rambly, occasionally chase a squirrel or two — and somehow still land on real, practical advice about getting clients, getting paid, managing money, and building something sustainable.

The rules weren't written for your brain. Let's change the rules.

Meet the Hosts

Jake Brown is a fractional revenue executive and business coach who works with business owners and founders on marketing, sales, and growth. He has ADHD. He runs a business. He's figured out a lot of this the hard way — and talks about it openly.

• Jake on LinkedIn: linkedin.com/in/airballoon

Caleb Bogia-Curles is a Certified Financial Planner who works with ADHD entrepreneurs. He has ADHD. He runs a business. He built his entire practice around the gap between standard financial advice and the way ADHD brains actually work.

• Caleb on LinkedIn: https://www.linkedin.com/in/%F0%9F%93%88caleb-bogia-curles-cfp%C2%AE-964823b8/

Resources:

https://www.focusedfounderswealthplanning.com/process

https://airballoonadvisory.com/

• https://airballoonadvisory.com/brainfrictionscore/

Struggling with days when everything feels off and executive functions are on vacation? In this episode, Jake and Caleb share personal stories, practical tools, and mindset shifts to help you manage burnout, boost productivity, and find grace during chaotic times. 

Main Topics:

• Common experiences of overwhelm and executive function fatigue
• How to recognize when you're bottoming out and strategies for jump-starting your day
• The value of the "one song" rule to overcome task inertia
• Body doubling and co-working as motivation tools
• The dopamine menu concept for immediate focus boosts
• Handling unpredictability: weather changes, kids, and schedule disruptions
• Prioritizing self-regulation over constant productivity
• The power of asking for help and setting realistic expectations
• Personal anecdotes about outdoor walks, water, and music for mental resets
• Neurodivergence insights: movement, risk, and sensory preferences

Doing Business with ADHD is for the late-diagnosed, the self-diagnosed, and the "I've always been this way but nobody ever called it anything" crowd — business owners and founders who are finally starting to understand why the standard playbook never quite worked for them.

Hosts Jake Brown and Caleb Bogia-Curles both have ADHD and both run businesses. Their conversations are honest, a little rambly, occasionally chase a squirrel or two — and somehow still land on real, practical advice about getting clients, getting paid, managing money, and building something sustainable.

The rules weren't written for your brain. Let's change the rules.

Meet the Hosts

Jake Brown is a fractional revenue executive and business coach who works with business owners and founders on marketing, sales, and growth. He has ADHD. He runs a business. He's figured out a lot of this the hard way — and talks about it openly.

• Jake on LinkedIn: linkedin.com/in/airballoon

Caleb Bogia-Curles is a Certified Financial Planner who works with ADHD entrepreneurs. He has ADHD. He runs a business. He built his entire practice around the gap between standard financial advice and the way ADHD brains actually work.

• Caleb on LinkedIn: https://www.linkedin.com/in/%F0%9F%93%88caleb-bogia-curles-cfp%C2%AE-964823b8/

Resources:

https://www.focusedfounderswealthplanning.com/process

https://airballoonadvisory.com/

• https://airballoonadvisory.com/brainfrictionscore/

In this episode, Jake and Caleb explore the concept of "changing the rules" to thrive as neurodivergent entrepreneurs, sharing personal stories, strategic insights, and unconventional paths to success. Whether you're looking for innovative investment ideas, business growth tactics, or ways to leverage your ADHD superpowers, this conversation offers fresh perspectives on navigating a world built for neurotypicals. Remember, the power lies in the willingness to experiment, pivot, and play outside the lines. Your neurodivergent perspective provides an edge—lean into it, and change your rules of success.

Main Topics:

• The "Cornucopia Play": Finding underserved markets and sidestepping competition through oblique strategies
• Case studies on unique pathways—military, business, and personal journeys—showing the power of pivoting and non-linear progress
• How ADHD tendencies can be assets for pattern recognition, outside-the-box thinking, and risk balancing
• The importance of experimentation in business, including sandboxing small risks and trusting your intuition
• Investment strategies that avoid herd mentality—favoring small caps, contrarian plays, and overlooked opportunities
• The role of externalizing decisions—outsourcing, automation, and collaborative risk-taking to reduce emotional burden
• Embracing the "what if" mindset to keep curiosity alive and push past traditional limits

Doing Business with ADHD is for the late-diagnosed, the self-diagnosed, and the "I've always been this way but nobody ever called it anything" crowd — business owners and founders who are finally starting to understand why the standard playbook never quite worked for them.

Hosts Jake Brown and Caleb Bogia-Curles both have ADHD and both run businesses. Their conversations are honest, a little rambly, occasionally chase a squirrel or two — and somehow still land on real, practical advice about getting clients, getting paid, managing money, and building something sustainable.

The rules weren't written for your brain. Let's change the rules.

Meet the Hosts

Jake Brown is a fractional revenue executive and business coach who works with business owners and founders on marketing, sales, and growth. He has ADHD. He runs a business. He's figured out a lot of this the hard way — and talks about it openly.

• Jake on LinkedIn: linkedin.com/in/airballoon

Caleb Bogia-Curles is a Certified Financial Planner who works with ADHD entrepreneurs. He has ADHD. He runs a business. He built his entire practice around the gap between standard financial advice and the way ADHD brains actually work.

• Caleb on LinkedIn: https://www.linkedin.com/in/%F0%9F%93%88caleb-bogia-curles-cfp%C2%AE-964823b8/

Resources:

https://www.focusedfounderswealthplanning.com/process

https://airballoonadvisory.com/

• https://airballoonadvisory.com/brainfrictionscore/

Feeling overwhelmed managing your finances as an entrepreneur with ADHD? This episode breaks down how to create a financial plan, find trustworthy advisors, and align your money with your goals — all in a relatable, down-to-earth way. Remember, the objective is to find a trustworthy guide who matches your personality and financial goals—don’t settle for less. Your future self will thank you.

Main Topics:

• The psychological barriers entrepreneurs with ADHD face around money and success
• How to recognize when it’s time for a financial plan
• Questions to ask when choosing a financial advisor, including red flags
• Why you should interview multiple advisors and seek fiduciary, fee-only professionals
• The importance of transparency, trust, and compatibility in financial relationships
• Practical steps for preparing for your first financial planning meeting
• How small, consistent reviews and updates can keep your financial goals on track
• The analogy of boats and vessels to conceptualize wealth and business assets
• How to avoid scams and find boutique, trustworthy financial advisors

Doing Business with ADHD is for the late-diagnosed, the self-diagnosed, and the "I've always been this way but nobody ever called it anything" crowd — business owners and founders who are finally starting to understand why the standard playbook never quite worked for them.

Hosts Jake Brown and Caleb Bogia-Curles both have ADHD and both run businesses. Their conversations are honest, a little rambly, occasionally chase a squirrel or two — and somehow still land on real, practical advice about getting clients, getting paid, managing money, and building something sustainable.

The rules weren't written for your brain. Let's change the rules.

Meet the Hosts

Jake Brown is a fractional revenue executive and business coach who works with business owners and founders on marketing, sales, and growth. He has ADHD. He runs a business. He's figured out a lot of this the hard way — and talks about it openly.

• Jake on LinkedIn: linkedin.com/in/airballoon

Caleb Bogia-Curles is a Certified Financial Planner who works with ADHD entrepreneurs. He has ADHD. He runs a business. He built his entire practice around the gap between standard financial advice and the way ADHD brains actually work.

• Caleb on LinkedIn: https://www.linkedin.com/in/%F0%9F%93%88caleb-bogia-curles-cfp%C2%AE-964823b8/

Resources:

https://www.focusedfounderswealthplanning.com/process

https://airballoonadvisory.com/

• https://airballoonadvisory.com/brainfrictionscore/

Discover how ADHD entrepreneurs can redefine accountability and freedom, turning potential pitfalls into empowering tools for sustained success. This episode explores practical strategies for creating supportive environments that foster growth without guilt or judgment.

Main Topics:

• The difference between freedom and flexibility in business ownership
• The emotional weight of traditional accountability systems
• Shifting from judgment to nudging: a better approach to accountability
• The importance of supportive ‘cheerleading’ in personal and professional growth
• Practical tools like co-working, public deadlines, and visual reminders for accountability
• The role of self-acceptance and tailored frameworks in achieving goals
• The impact of physical sensations and emotional triggers on accountability
• How to create a culture of encouragement versus control

Doing Business with ADHD is for the late-diagnosed, the self-diagnosed, and the "I've always been this way but nobody ever called it anything" crowd — business owners and founders who are finally starting to understand why the standard playbook never quite worked for them.

Hosts Jake Brown and Caleb Bogia-Curles both have ADHD and both run businesses. Their conversations are honest, a little rambly, occasionally chase a squirrel or two — and somehow still land on real, practical advice about getting clients, getting paid, managing money, and building something sustainable.

The rules weren't written for your brain. Let's change the rules.

Meet the Hosts

Jake Brown is a fractional revenue executive and business coach who works with business owners and founders on marketing, sales, and growth. He has ADHD. He runs a business. He's figured out a lot of this the hard way — and talks about it openly.

• Jake on LinkedIn: linkedin.com/in/airballoon

Caleb Bogia-Curles is a Certified Financial Planner who works with ADHD entrepreneurs. He has ADHD. He runs a business. He built his entire practice around the gap between standard financial advice and the way ADHD brains actually work.

• Caleb on LinkedIn: https://www.linkedin.com/in/%F0%9F%93%88caleb-bogia-curles-cfp%C2%AE-964823b8/

Resources:

https://www.focusedfounderswealthplanning.com/process

https://airballoonadvisory.com/

• • https://airballoonadvisory.com/brainfrictionscore/

In this episode, Jake Brown and Caleb Bogia-Curles explore how recognizing and honoring the natural highs and lows — likened to ocean tides — can transform how adults with ADHD manage their energy, tasks, and relationships. They share personal stories, practical strategies, and mental models to help you live more in sync with your rhythms instead of fighting them.

Main Topics Covered:

• The analogy of ADHD as ocean tides: high tide (productive moments) and low tide (recovery or low energy periods)
• How the expectation of constant productivity leads to burnout and guilt
• Practical tools like mapping tides with worksheets to identify personal rhythms
• Planning weekly tasks around high and low tides for more realistic goal-setting
• Importance of protecting low tides for recovery and overall performance
• Applying the concept to relationships, family, and self-care
• The impact of societal expectations on perceptions of productivity and worth

Doing Business with ADHD is for the late-diagnosed, the self-diagnosed, and the "I've always been this way but nobody ever called it anything" crowd — business owners and founders who are finally starting to understand why the standard playbook never quite worked for them.

Hosts Jake Brown and Caleb Bogia-Curles both have ADHD and both run businesses. Their conversations are honest, a little rambly, occasionally chase a squirrel or two — and somehow still land on real, practical advice about getting clients, getting paid, managing money, and building something sustainable.

The rules weren't written for your brain. Let's change the rules.

Meet the Hosts

Jake Brown is a fractional revenue executive and business coach who works with business owners and founders on marketing, sales, and growth. He has ADHD. He runs a business. He's figured out a lot of this the hard way — and talks about it openly.

• Jake on LinkedIn: linkedin.com/in/airballoon

Caleb Bogia-Curles is a Certified Financial Planner who works with ADHD entrepreneurs. He has ADHD. He runs a business. He built his entire practice around the gap between standard financial advice and the way ADHD brains actually work.

• Caleb on LinkedIn: https://www.linkedin.com/in/%F0%9F%93%88caleb-bogia-curles-cfp%C2%AE-964823b8/

Resources:

• ADHD Tides Worksheet
• https://www.focusedfounderswealthplanning.com/process
• https://airballoonadvisory.com/
• https://airballoonadvisory.com/brainfrictionscore/

Unlock practical insights into how ADHD influences hidden costs in daily life and business, and learn strategies to reduce these extra expenses and frustrations. In this episode Jake and Caleb explore real-life examples and actionable tips to plan ahead and mitigate ADHD-related challenges.

Main Topics:

• The concept of ADHD tax: definitions and personal examples
• How ADHD affects financial management, subscriptions, and time
• Practical strategies for ADHD tax planning: automations, delegation, and mindset shifts
• The importance of proactive planning and risk minimization
• Emotional aspects: shame, humor, and building a supportive environment
• Reflection on how societal rules and systems can create additional “ADHD taxes”
  

Doing Business with ADHD is for the late-diagnosed, the self-diagnosed, and the "I've always been this way but nobody ever called it anything" crowd — business owners and founders who are finally starting to understand why the standard playbook never quite worked for them.

Hosts Jake Brown and Caleb Bogia-Curles both have ADHD and both run businesses. Their conversations are honest, a little rambly, occasionally chase a squirrel or two — and somehow still land on real, practical advice about getting clients, getting paid, managing money, and building something sustainable.

The rules weren't written for your brain. Let's change the rules.

Meet the Hosts

Jake Brown is a fractional revenue executive and business coach who works with business owners and founders on marketing, sales, and growth. He has ADHD. He runs a business. He's figured out a lot of this the hard way — and talks about it openly.

• Jake on LinkedIn: linkedin.com/in/airballoon

Caleb Bogia-Curles is a Certified Financial Planner who works with ADHD entrepreneurs. He has ADHD. He runs a business. He built his entire practice around the gap between standard financial advice and the way ADHD brains actually work.

• Caleb on LinkedIn: https://www.linkedin.com/in/%F0%9F%93%88caleb-bogia-curles-cfp%C2%AE-964823b8/

Resources:

https://www.focusedfounderswealthplanning.com/process

https://airballoonadvisory.com/

• • https://airballoonadvisory.com/brainfrictionscore/

In this episode, Jake and Caleb share their journey of launching something new from a neurodivergent perspective—breaking conventional rules and embracing imperfection. They discuss how ADHD influences their approach, the importance of momentum over perfection, and practical tips to get started despite doubts or obstacles.

Main Topics:

• Overcoming the mental hurdles of starting a new project with ADHD
• How to simplify planning and reduce over-polishing
• The power of batching and accountability in maintaining momentum
• Building in secret vs. building in public: pros and cons for neurodivergent entrepreneurs
• Celebrating milestones and anchoring success with intentional toasts
• Emphasizing the importance of community, accountability nudges, and partnership
• Reframing rejection sensitivity and building in private to protect your energy
• The "who not how" framework: finding companions to facilitate action
• Embracing messy, imperfect progress as a form of authenticity and growth

Doing Business with ADHD is for the late-diagnosed, the self-diagnosed, and the "I've always been this way but nobody ever called it anything" crowd — business owners and founders who are finally starting to understand why the standard playbook never quite worked for them.

Hosts Jake Brown and Caleb Bogia-Curles both have ADHD and both run businesses. Their conversations are honest, a little rambly, occasionally chase a squirrel or two — and somehow still land on real, practical advice about getting clients, getting paid, managing money, and building something sustainable.

The rules weren't written for your brain. Let's change the rules.

We delve into the hierarchy of financial needs, the messy journey of building a business, the importance of tax planning, and the strategic use of debt and financial leverage. We emphasize the need for strategic decision-making and the importance of seeking professional advice in financial matters. The conversation covers a range of financial topics relevant to business owners, including ADHD budgeting, strategic debt, entrepreneurship through acquisition, diversification, retirement planning, business valuation, legacy and exit planning, and financial planning with tax considerations. We emphasize the importance of understanding and addressing these financial aspects to build and protect business wealth effectively.

Takeaways

• Hierarchy of financial needs
• Importance of tax planning ADHD budgeting and shiny object syndrome impact financial decision-making.
• Strategic debt and business growth require careful planning and risk management.

Doing Business with ADHD is for the late-diagnosed, the self-diagnosed, and the "I've always been this way but nobody ever called it anything" crowd — business owners and founders who are finally starting to understand why the standard playbook never quite worked for them.

Hosts Jake Brown and Caleb Bogia-Curles both have ADHD and both run businesses. Their conversations are honest, a little rambly, occasionally chase a squirrel or two — and somehow still land on real, practical advice about getting clients, getting paid, managing money, and building something sustainable.

The rules weren't written for your brain. Let's change the rules.

Meet the Hosts

Jake Brown is a fractional revenue executive and business coach who works with business owners and founders on marketing, sales, and growth. He has ADHD. He runs a business. He's figured out a lot of this the hard way — and talks about it openly.

• Jake on LinkedIn: linkedin.com/in/airballoon

Caleb Bogia-Curles is a Certified Financial Planner who works with ADHD entrepreneurs. He has ADHD. He runs a business. He built his entire practice around the gap between standard financial advice and the way ADHD brains actually work.

• Caleb on LinkedIn: https://www.linkedin.com/in/%F0%9F%93%88caleb-bogia-curles-cfp%C2%AE-964823b8/

Resources:

https://www.focusedfounderswealthplanning.com/process

https://airballoonadvisory.com/

• https://airballoonadvisory.com/brainfrictionscore/