Episode 137: Freedom business reality: from agency life to freedom freelancing with Jake Madoff

Meet freedom business owner Jake

Jake Madoff is a full stack growth marketer specializing in paid media, SEO, and funnel optimization. What began as self-teaching web design for his own e-commerce business in 2014 evolved through co-founding a trade and barter app startup, to spending five years scaling a company’s ad spend from $300K to $2 million monthly.

During COVID, Jake transitioned to full-time freelancing, where he now helps businesses across diverse industries—from e-commerce to legal to B2B SaaS—grow through strategic digital marketing.

Based in Manhattan, he represents a new generation of marketing professionals who’ve learned their craft not through traditional education but through hands-on experimentation, adaptation, and saying “yes” to new opportunities before they felt fully ready.

“Some people just aren’t really wired to be managed. I find myself so much more productive if I am telling myself what to do versus other people telling me what to do.”

Key takeaways from our freedom chat with Jake:

➡️ The psychological freedom effect: Even though entrepreneurs often work more hours than employees, having control over when and how you work creates a profound psychological freedom that transforms your relationship with work.

➡️ Say Yes, then learn to say No: Early in your entrepreneurial journey, saying yes to opportunities—even ones you’re not fully prepared for—forces rapid growth and skill development. As you mature, learning when to say no becomes equally critical.

➡️ The hidden economics of freelancing: Agency marketers managing six clients while making $60-80K could potentially earn $15K monthly by taking those same clients freelance—a dramatic shift in income potential that’s rarely discussed in traditional career paths.

➡️ Sustainable vs. unsustainable business models: Some business models (like dropshipping) have shorter shelf lives due to easy replication, while others (like growth marketing) offer medium-term sustainability before potential AI disruption—choose wisely based on your timeline.

➡️ The self-development accelerator: Entrepreneurship functions as “a self-fulfilling journey on steroids,” forcing rapid personal growth in areas like boundary-setting, communication, and self-discipline that transform far more than just your income.

Connect with Nienke Nina

More digital nomad tips and life advice via instagram @digitalnomadsdaily

Connect with Nienke Nina on LinkedIn @Nienke Nina Keizer

Find Nienke Nina on Instagram @growwithnienkenina

Connect with Jake

Visit on LinkedIn @Jake Madoff

Website: www.jakemadoff.io

136: When your Freedom Lifestyle no longer feels free with Nienke Nina

Ever feel like the freedom lifestyle you chased so hard suddenly doesn’t feel freeing anymore?

Nienke Nina talks about her personal journey through an identity crisis after five years as a digital nomad, falling in love, settling down, and questioning everything she built her brand on. She dives deep into what freedom really means beyond the Instagram-perfect shots of laptops on beaches, and why creating true freedom in your life is both painful and beautiful.

If you’ve ever felt out of alignment with your business, lifestyle, or identity, this raw conversation will help you reconnect with what freedom truly means for YOU.

“I focus more on alignment. I say ‘aligned freedom business’ because I see so many people copying someone else’s freedom business because they think that’s freedom.”

Key takeaways from our freedom life & business episode:

➡️ Freedom is about Aligned Expressions: True freedom comes from creating expressions of your life (business, relationships, location) that are in alignment with who you are. When these expressions aren’t aligned, you’ll feel friction, self-doubt, and may fall out of love with things you used to enjoy.

➡️ Freedom isn’t static: Your freedom goals will evolve over time. What feels freeing now may not feel the same next year. Freedom requires constant exploration and curiosity about what works for you in each season of life.

➡️ How the Digital Nomad identity can be limiting: The stereotype of a digital nomad (constant travel with a laptop) is just one expression of freedom. There are countless ways to create freedom sensations in your life without fitting this narrow definition.

➡️ Creating freedom takes intentional ongoing work: Building a freedom lifestyle requires deep self-reflection, strategy, and implementation. It’s not a quick fix but a continuous process of alignment and realignment as you grow.

➡️ Business Alignment requires regular check-ins: When your business no longer feels enjoyable, a thorough alignment audit can help you understand what’s working, what’s not, and how to create a strategy that brings back those freedom sensations.

Connect with Nienke Nina

More digital nomad tips and life advice via instagram @digitalnomadsdaily

Connect with Nienke Nina on LinkedIn @Nienke Nina Keizer

Find Nienke Nina on Instagram @growwithnienkenina

Episode 135: Creating a Powerful Personal Brand for Digital Nomad with Marina

Meet digital nomad Marina

The first Egyptian in the show, Marina, who has been embracing the digital nomad lifestyle for two years, after starting her journey as a creative freelancer back in 2015.

Marina currently earns money as a personal brand coach due to her love for coaching, design, writing, and photography. No wonder, she has successfully turned her passions into a thriving online business.

As Nienke Nina looks back on their conversation, it is amazing how pertinent their points are up to date – the challenges of pivoting your business, personal branding, overcoming mindset struggles, and the realities of solopreneurship. Bringing with us years of experience, Nienke Nina and Marina talked about unpopular truths about building your personal brand and everything in between.

“My responsibility is to show up as true to myself as possible because that is how I can sustain my business”

Key takeaways from our freedom chat with Marina:

➡️ Be in alignment with your personal brand: Building your own personal brand takes honesty and vulnerability.

➡️ Have a mentor to fasten the process: Marina shared how her journey changed when she acquired a mentor in her journey.

➡️ Get rid of things that are not working: Your energy is important so make sure you’re putting it into something worth it.

➡️ Action > manifestation: Manifesting alone is not enough and sustainable for the long term so start taking action alongside manifesting.

➡️ There is no one-size-fits-all strategy: Marina talked about how it’s important to remember that everything takes time and the idea of a one-size-fits-all strategy is completely a myth.

Connect with Nienke Nina

More digital nomad tips and life advice via instagram @digitalnomadsdaily

Connect with Nienke Nina on LinkedIn @Nienke Nina Keizer

Find Nienke Nina on Instagram @growwithnienkenina

Meet digital nomad Marina

Find on LinkedIn here

Instagram: @vivaciouslymarina

Website 🔗 livinvivaciously.com

Episode 134: Why Your Freedom Business Doesn’t Feel Like Freedom with Nienke Nina

“When things are in alignment, they flow and they just flow so well.

True Freedom & Alignment

As digital nomads, despite our consistent travels and changing places, we also want a sustainable and fulfilling lifestyle. That brings us to this episode of being in alignment with your business. We have repeatedly talked about in our podcast why alignment is important – imagine if your business activities align with your values, passions, and personal goals, you experience greater fulfilment and motivation in your life for sure!

Key takeaways from Nienke Nina

5 things you learn in this Digital Nomads Daily episode

➡️ What is a freedom business like: Aligning your business with personal joy and values can give you higher changes for lasting success and fulfilment as a digital nomad.

➡️ You can align your passion with profit: It is possible to build a business centred around your passion and skills.

➡️ Overcoming entrepreneurial challenges can be fun: There are very practical tips to handle the ups and downs of entrepreneurship while enjoying every bit of it.

➡️ Thriving in growth zones: You will learn that by embracing discomfort and growth zones, you can improve your personal and professional development in the nomadic lifestyle.

➡️ Why clarity is important in your business: Practice the habit of asking yourself introspective questions to clarify your business direction, reduce overwhelm, and build a more purpose-driven approach.

Connect with our Nienke Nina and our guests

Your host Nienke Nina

More digital nomad tips and life advice via instagram @digitalnomadsdaily

Connect with Nienke Nina on LinkedIn @Nienke Nina Keizer

Find Nienke Nina on Instagram @nienkeninatravels

Other episodes you might like:

🎧  Episode #104: How To Live a More Fulfilling Digital Nomad Lifestyle with Bianca

🎧  Episode #129: The Nomadic Entrepreneur Journey to Find True Alignment & Fulfillment Unpacked with Generation Nomads

🎧  Episode #130: Finding Purpose & Alignment Through Conscious Co-Living & Retreats with Digital Nomad Anja

Episode 133: Tips on How to Choose Your Next Digital Nomad Event

“Intentionality is key. Going to events with a clear purpose helps you get the most out of your experience and stay aligned with your goals.”

Attending Digital Nomad Events

Nienke Nina has immersed herself in a lot of digital nomad events over the years, from large conferences to intimate retreats and vibrant festivals. Her experience attending events help her to connect with various nomads and experts around the world. Through these events, Nienke Nina has gained a deep understanding of the challenges and opportunities in the nomadic lifestyle which she passionately shares with her audience to help them go through their digital nomads journey.

Key takeaways from this episode about digital nomad events

5 things you learn in this Digital Nomads Daily episode

➡️ Choosing the right nomad events: How to select events that align with your interests and goals to maximise your experience and avoid overwhelm.

➡️ Embracing intentionality: Why going to events with clear intentions can definitely enhance your experience and provide a better return on investment.

➡️ Balancing personal and professional life: How can digital nomads maintain their well-being while attending events

➡️ Leveraging event opportunities: How to use events to expand your network, build connections, find new clients, and create valuable business collaboration.

➡️ Considerations in choosing the right event: There are things worth considering like personal interests, type of events, expected community, location, personal capacity and event logistics.

Connect with our Nienke Nina and our guests

Your host Nienke Nina

More digital nomad tips and life advice via instagram @digitalnomadsdaily

Connect with Nienke Nina on LinkedIn @Nienke Nina Keizer

Find Nienke Nina on Instagram @nienkeninatravels

Other episodes you might like:

🎧  Episode #114: Why You Need to Prioritize In-Person Gatherings

🎧  Episode #120: Reflections from Minoma Festival 2023 for Mindful Nomads with Nienke Nina

🎧  Episode #129: The Nomadic Entrepreneur Journey to Find True Alignment & Fulfillment Unpacked with Generation Nomads

Episode 132: Remote Entrepreneur & Freedom Deep Dive with Alex from Jobgether

“Don’t expect to become rich overnight as a freelancer or entrepreneur. Instagram isn’t reality; you have to work hard every day.”

Meet Jobgether Co-Founder Alex

Nienke Nina is interviewing Alex Hernandez, who has been living the digital nomad lifestyle for four years. Alex started his journey just before the lockdown as he moved from Paris to Madrid.

Alex is earning his money primarily through his startup, Jobgether, which he co-founded. More than that, he occasionally takes on freelance projects in sales and human resource, although his main focus remains on Jobgether.

We cover a range of topics and challenges in this episode such as the realities of building a startup, the misconceptions about the digital nomad lifestyle, and practical tips for maintaining work-life balance and staying productive at the same time.

Key takeaways from from Alex’s interview about remote entrepreneurship

5 things you learn in this Digital Nomads Daily episode

➡️ Building a startup from scratch: Have a glimpse of Alex’s journey of founding Jobgether during the lockdown and the challenges he faced in the early days.

➡️ The reality of digital nomadism: Why most digital nomads don’t live the “tech guy on a beach in Bali” lifestyle and how to create your own path.

➡️ Balancing work and life: Alex’s secrets to maintaining a healthy work-life balance while running a successful startup and traveling at the same time.

➡️ The truth about financial freedom: Misconceptions about financial freedom in entrepreneurship and why it’s crucial to have realistic expectations in this industry.

➡️ Practical productivity tips: Get Alex’s go-to strategies for staying productive and motivated, even during the toughest days of his entrepreneurial life.

Connect with our Nienke Nina and our guests

Your host Nienke Nina

More digital nomad tips and life advice via instagram @digitalnomadsdaily

Connect with Nienke Nina on LinkedIn @Nienke Nina Keizer

Find Nienke Nina on Instagram @nienkeninatravels

Meet digital nomad Alex

Find on LinkedIn here

Instagram: @jobgether

Website 🔗 www.jobgether.com

Other episodes you might like:

🎧  Episode #22: Facing The Realities Of Online Entrepreneurship with Anne

🎧  Episode #28: How Digital Nomads Can Become Successful Entrepreneurs With John

🎧  Episode #38: How Leaders Can Strengthen Remote Company Culture With Jürgen