E15 Inside the Mind of a Serial Founder with 3 Exits

Episode Summary
There are plenty of problems to solve in the ecommerce space. As the market gets larger it also gets more complex with new problems to solve arriving almost daily. Throughout my career in ecommerce, I have come across a “mafia” of founders - that is people who see and experience the problems firsthand, build a software solution to solve it, get the business to the right scale for an exit; rinse, and repeat. We are oversimplifying some of the complexities, but it can never be understated how much focus and commitment is required to build and exit a software business in any market AND do it more than once.
In this episode of In/organic, I was joined by Chad Rubin, founder of commerce ecosystem notables including Prospershow, Skubana, Sellers Choice, and more recently Profasee. Every business Chad has built was started to solve a problem he experienced as an online retailer and whereby he brought the solution to market to help thousands of online sellers thrive. In this episode, I explore with Chad the formula for success as a repeat founder and his experiences and learnings along the way of building and exiting thoughtfully.
Takeaways
- Chad's approach to building businesses involves identifying real pains in commerce, experiencing those pains directly, and building companies around them.
- The decision to sell a business involves considering market trends, acquisition behavior, and economic impact, as well as ensuring a successful outcome for stakeholders and employees.
- The sale process requires careful consideration of the vision and execution of the acquiring party, as well as the deal structure and post-sale arrangements.
- Chad's journey highlights the importance of perseverance, non-consensus thinking, and proving oneself right in the face of skepticism from investors and VCs. Life after a successful exit may not bring the expected life-changing outcomes.
- Balancing work and personal life is essential for long-term success and fulfillment.
- Market opportunities in e-commerce are evolving, with a focus on multichannel and niche markets.
- The entrepreneurship journey involves continuous learning and adaptation, focusing on personal growth and well-being.
Chapters
00:00 Introduction
02:59 Chad Rubin's background
04:16 Building a business
06:53 Strategic thinking about outcomes
09:00 Learnings from selling a business
12:43 The decision to sell
17:42 Running the sale process
22:56 Insights for founders selling a business
25:42 Experiences as a serial founder and exiter
30:41 Optimizing for platforms of varying maturity levels
34:39 Maximizing the outcome
35:47 The pattern of building and selling
38:47 Advice for aspiring serial founders
Connect with Christian & In/organic Podcast
Christian's LinkedIn: / hassold
In/organic on LinkedIn: / inorganic-podcast
Connect with Chad Rubin on LinkedIn
/ itschadrubin