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Jesse Lee
"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.
JD & Liza Kameen
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.
Maulik Patel
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.
Taj Smith
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.
Kristen Gardner & Lance Lemon
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.