Exploring passions and maintaining the relationships along the way has been at the core of Sean Moran’s entrepreneurial journey. Sean is the owner of Dashing Chicago, a luxury footwear retailer located in downtown Chicago. In our conversation, we dive into Sean’s experience opening and running stores before he finally opened Dashing in Spring 2021. He highlights the importance of persistence, patience, and relationships. All of which have enabled Dashing to be the premier Alden and Edward Green retailer in the Midwest.

DashingChicago.com

Learning how to be an effective CEO is a different growth journey than being an entrepreneur. Rob Volk leads Foxbox Digital, a rapidly growing digital product agency. In this conversation we explore Rob’s learnings from transitioning from co-founder and CTO in his previous role to founder and CEO with Foxbox. Through this conversation, we learn about how important of branding your culture and lead with your company’s values. This is a great episode for future CEOs.

Foxbox.com

Sometimes, the critical first step to launching a business is having the audacity to believe that you can be successful. George Davis Jr., the owner of Muse Coffee Studio in Chicago, shares his entrepreneurial journey and the work it took to achieve the milestone of launching his small business. Starting with an abstract vision for a soulful coffee studio, Muse is an art gallery styled coffee mosaic in Chicago's Near West Side neighborhood. In our conversation we explore the feelings of self-doubt, get to the starting line, identifying what truly differentiates your product, and more.

MuseCoffeeStudio.com

An aspiring professional athlete turned YouTuber, Ken Jee truly embodies the idea of making a living doing what you love. In our conversation, Ken talks about how his passions have led his business interests, and how that mindset has expanded his definition of "entrepreneurship". Additionally, we talk about the power of repetitions and the importance of embracing "small, acceptable failures". We explore the feeling of imposter syndrome and how consistently seeing personal growth through his videos helps him combat this feeling.

Ken Jee's YouTube Channel

"Experience is the teacher of all things" - Julius Caesar

Jesse Lee has spent much of his career launching and growing startups. He has started five or six different software businesses, with one going public on the NASDAQ in October 2016 at a $770 million market capitalization. Through those experiences, he's learned a lot about what he calls "the sickness of entrepreneurship". In our conversation, we explore his perspective on finding the right cofounders, getting real, honest feedback, and the never-ending balance of timeliness and patience. His humility and genuineness shine through as he shares his lessons learned over the years.

BrooklynVA.com

In attempt to commission the painting of a photo from their honeymoon, JD & Liza Kameen unknowingly stumbled upon an opportunity to start their own business. Paintru, a startup that makes it easy to commission art, has received recognition in numerous publications and successfully completed a fundraising round. I sit down with these cofounders to talk about their experience launching Paintru and how they've managed the risk of this venture. These new parents are running Paintru while maintaining their respective, full-time careers. Additionally, Liza is completing business school part-time and JD is finishing his time as a Marine officer. We discuss the importance of knowing what "fills your cup" and managing the constant demands on your time and energy as an entrepreneur.

Paintru.com

What did entrepreneurship do for you? For Maulik Patel, a passion for environmental sustainability led to him joining a startup and eventually co-founding a solar energy performance software company. The learnings from this experience opened new career opportunities for him that previously wouldn’t have existed. In this episode, we talk about the importance of identifying the unique value you provide to the market and achieving your minimal viable product as efficiently as possible.

Through self-awareness, a helpful skills assessment test, and a desire to make more money, Taj Smith opened his own law firm 9 years ago. While embracing the discomfort of entrepreneurship, The Smith Law Group continues to thrive with limited marketing and an endless supply of lawyers within Chicago. In this episode we explore Taj's experience of being a black lawyer and a "solopreneur". Our discussion highlights the rewards and the anxieties that entrepreneurs face on a regular basis. Additionally, we talk about ways to find balance and manage the mental stress that comes with owning your own business.

After a night out in NYC, lifelong friends Kristen Gardner and Lance Lemon were tossing around ideas on what to name their future, Richmond-based wine shop. As this vision started taking shape, the COVID-19 pandemic forced them to rethink their plans to sign a lease. While Kristen worked full-time and Lance started a family, these co-founders pivoted and transformed their business overnight. RichWine would now be a boutique, online wine shop providing same-day wine delivery service. 

In this conversation, we explore the challenges of starting a business while maintaining a full-time job, going into business with a close friend, and their approach to jointly making decisions. 

RichWineRVA.com