Entrepreneur and investor Justin Duke discusses his journey from working at Stripe to starting his own company and acquiring five software businesses. Topics include the challenges of buying software businesses, evaluating factors in acquisitions, determining value and revenue generation patterns, advice for buying a digital company, building a business portfolio, and a profound book recommendation.
Align personal goals and values with business ventures.
Be selective and say no to opportunities that do not align with priorities.
Prioritize activities that bring joy and fulfillment in order to create a balanced and fulfilling lifestyle.
Deep dives
Justin's Journey into Third South Capitol
Justin Duke shares his background in big tech and startups before discovering his passion for working with independent businesses. He explains his desire to build and operate businesses that are healthy, profitable, and stable, rather than focusing on high-growth potential. Justin and his partners started Third South Capitol, a fund oriented around acquiring and stewarding small businesses. They acquired five businesses, each fitting their profile of being small and operated by founders looking to move on. Justin discusses the process of sourcing, closing, onboarding, and operating these businesses and highlights the fulfillment and growth they have experienced.
The Importance of Matching Goals and How to Find the Right Size of Acquisition
Justin emphasizes the importance of aligning personal goals and values with the businesses one acquires. He mentions the need to evaluate one's priorities and define what they want to achieve in the long term. He shares that their initial goal with Third South Capitol was to determine if they enjoyed the venture and could sustainably operate it. Having achieved that, they now aim to scale their portfolio with a focus on larger acquisitions that align with their values. While financial returns are considered, impact and fulfillment take precedence over business size.
Balancing Third South Capitol and Buttondown
Justin discusses how he balances his role at Third South Capitol with his other project, Buttondown. He emphasizes the importance of sustainability and prioritizing time for activities that bring fulfillment. Justin views work as a blend with other aspects of life, focusing on doing interesting tasks that align with personal interests. While he acknowledges the risks involved, he believes in creating a balanced and fulfilling lifestyle that allows for freedom and agency over how time is spent.
The Benefits of Tracking Media Consumption
Justin shares his practice of tracking and documenting his daily media consumption, including books, movies, and video games. He finds it valuable to have a record of what he consumes and his thoughts about each piece. Tracking allows him to reflect on trends and themes over time and serves as a time capsule for past interests and experiences. Justin believes that mindful media consumption leads to more rewarding and fulfilling experiences and encourages intentionality in choosing what to consume.
Lessons Learned and Insights Gained
Justin imparts several lessons and insights from his experience with Third South Capitol. He highlights the importance of aligning personal goals and values with one's business ventures. He emphasizes the need to be selective and say no to opportunities that do not align with one's priorities. He also notes the significance of evaluating code bases when acquiring businesses and the impact they can have on future improvements. Finally, Justin encourages individuals to be mindful of how they spend their time and to prioritize activities that bring joy and fulfillment.
I was curious about buying software-based businesses so I reached out to Justin Duke who started Third South Capital. We talk about his journey from working at Stripe to starting his own company to acquiring five software companies.
