Joel Stevenson on Entrepreneurship, Acquisitions, and the Power of Humor

Welcome to an exclusive insight into the world of entrepreneurship and the art of acquiring businesses. Today, we sit down with Joel Stevenson, the GM of brand direct brands at Vendasta, who shares his remarkable journey from scaling a start-up to managing the sale of Yesware, and offers valuable insights into how entrepreneurs can invest in themselves to drive success.

Speaking about his career, Joel Stevenson reflects, “I started my career in sales and was redirected by this notion that no matter what I do, I’m in sales – a good place to start a career if you don’t have a very strong point of view about something else you’re gonna do.”

Joel’s journey took him through diverse roles, wherein he played a pivotal role in building a B2B business for Wayfair and ultimately guiding the company through its transition into a publicly traded entity.

Tune in to the Invest in Yourself podcast featuring Paul Better and Paul Stevens, discussing entrepreneurship and investments.

“The most important thing you can do to get your company sold is to make sure that it’s a company worth buying.”

The acquisition process of Yesware revealed challenges and pivotal decisions. Joel emphasizes, “Some entrepreneurs are pathologically optimistic. That’s a great thing about entrepreneurs. But being honest with yourself about where things are at is important, with the opportunity cost of your time in mind.”

Discussing his future plans, Joel shares, “I increasingly lean towards starting my own business. It’s a tremendous time for entrepreneurship, and I think you can take things pretty far now with a lot less capital and people than before.”

The conversation also touched upon technological advancements in business. Joel reveals his use of AI, stating, “If we beat a number by 10% or we drop a number by 10%, maybe it doesn’t matter that much. The trend’s important. What you’re trying to build together is important.”

As we wrap up our insightful conversation with Joel Stevenson, we are reminded of the power of mindfulness and the importance of not taking life too seriously. Joel states, “I’ve had the benefit of spending more time with a mindfulness and meditation practice. There is so much disruption happening, and it’s a pretty cool time to start a business.”

In conclusion, Joel’s journey illustrates not only the strategic aspects of entrepreneurship and acquisitions but also the power of investing in oneself and embracing the unpredictable nature of business. Aspiring entrepreneurs, take note – the power to succeed lies within your ability to adapt and invest in your personal and professional growth.

In the words of Joel Stevenson, “It’s a very freeing feeling to just lighten up a little bit and realize that you’ve got it so much better than so many other people.”

So, remember, entrepreneurs, always invest in yourself.

That’s all for today, folks. Until next time, Phil Better

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Phil Better

Phil Better aka The Podcast Mogul

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