A Relationship First Approach to Business Building with Adam ‘Smiley’ Poswolsky
I recently had the pleasure of interviewing Smiley Poswolsky on my podcast where he shared his journey from government employee to successful keynote speaker and author. He shares five hard earned lessons in creative entrepreneurship which offer wise words for anyone considering a major career pivot or building a creative business.
At age 30, Smiley made a decision that would transform his life: he left his stable government job to pursue more meaningful, creative work. With no concrete plan except a desire for change, he packed his bags for San Francisco. What started as a simple blog documenting his career transition eventually led to his first self-published book, which opened unexpected doors into the world of professional speaking.
The Evolution of a Speaking Business
One of the most fascinating aspects of Smiley's story is how his business model evolved organically. He initially focused on selling books However, he soon realized that selling $15 books wouldn't create the sustainable income he needed. The pivot point came when he came off the high of his TED talk and realized how much it energized him. When he started to see corporate interest in millennial workplace trends he found his offer sweet spot.
Today, Smiley delivers around 50 paid keynotes annually, focusing on workplace culture, belonging, and connection. This evolution taught him a crucial lesson about business adaptability: as he puts it, "stay in your lane but keep the windows open." While maintaining his core expertise, he remained open to new opportunities and directions.
The Power of Patience and Community
Perhaps the most striking takeaway from our conversation was the importance of patience in building a successful speaking business. It took Smiley over a decade to reach his current level of success – a reminder that overnight success stories are often myths that gloss over the reality of persistent, gradual growth.
Smiley excels at building deep relationships and community. The majority of his speaking engagements come through referrals and connections built over years. This approach – prioritizing relationship-building over aggressive marketing – has created a sustainable business model based on trust and genuine connection. It’s one that we often forget is possible (and effective) with so much pressure going toward gaining mass followership on social media.
Lessons for Aspiring Speakers and Entrepreneurs
Through his journey, Smiley has learned several key principles that resonate with anyone building a creative business:
1. Quality Over Quantity: Instead of chasing constant output, focus on creating exceptional content and experiences that truly impact your audience.
2. Define "Enough": Set clear boundaries around what success means to you to avoid the trap of constant striving and eventual burnout.
3. Embrace the Challenges: The speaking business comes with its unique hurdles – from lonely travel to administrative tasks and the pressure to stay relevant. Acknowledging these challenges helps to emotionally fortify yourself for them.
Final Thoughts
Smiley's journey from government worker to professional speaker isn't just a career change story – it's a masterclass in building a sustainable creative business. His experience shows that with patience, authentic relationship-building, and a willingness to evolve while staying true to your core message, you can build a successful speaking business establishing yourself as an expert in a coveted niche.
You can find Smiley at:
Website: https://www.smileyposwolsky.com/
IG: https://www.instagram.com/whatsupsmiley/
Substack: https://substack.com/@friendswithsmiley
