Today we are talking to entrepreneur and best-selling author, Jeff Wald. Jeff has started and exited a couple businesses, both successfully and unsuccessfully. Learning valuable lessons in business and in life, Jeff keeps moving forward. With a passion for investing in startups, Jeff has helped many new entrepreneurs. He also offers wealth management advice through his latest company, Bento Engine.

A Traditional Approach To Business

Jeff took the traditional route of Harvard Business School and a job at JPMorgan. He ended up finding himself as Vice President of a private equity firm, where he would often fawn over new startups. The head of the company told Jeff that if he was that enamored, that he should start his own company and offered backing. Jeff would go on to start his own company, but he chose to self fund it. It was a product sharing network called Spinback. It was a way for retailers and brand owners to share their products through the social web.

Why You Should Address Issues Early On

There were three co-founders for Spinback, including Jeff. He originally thought he would just help fund the company, but was invited to be a part of it. Jeff says he did end up funding it also, while the other two founders sued each other. Jeff regrets spending so much time trying to keep everyone together. He says by the time he realized one of them needed to go, they were both already dug in, and attorneys were involved. So, the company went broke, and Jeff went broke right along with it. He didn’t feel like the investors should pay for the company's failure because of the other two founders. Jeff learned a valuable lesson from that failed exit, and that was to always address issues early on.

First And Biggest Hit

When he received a call from his mom offering him a room back home, Jeff knew it was over. He had gone to all the right schools, put in the hard work, the time, and the money, yet here he was left with nothing. This sent Jeff into a pretty debilitating depression. It was his first and biggest hit. It took some time, but Jeff eventually picked himself up and dusted himself off.

Taking Good Advice

When he was ready to start another company, Jeff says he was involved in essentially a restart of the last concept. He says two new entrepreneurs took the driver’s seat while he remained in the background. He gave them code, ideas, and a little funding, and the two built up the company and sold it to BuddyMedia for tens of millions of dollars in BuddyMedia stock. The deal almost didn’t go through, however, when Jeff marched into the owner's office and demanded it be cash and not stock. Jeff felt the stock was overvalued as it was. The owner simply told him, as a friend, he was wrong, and he’d want to take the stock. Taking her advice, the deal went through. Five months later, BuddyMedia got bought out for $800million.

Knowing What You Know Now, What Would You Tell Yourself Ten Years Ago?

Ten years ago, Jeff was just starting his WorkMarket journey. He says he remembers being so scared to fail again. He would tell himself he could do it. To put in the hard work, and it’ll all be okay.

What Jeff’s Working On Now

After the last exit, Jeff was able to finish his book, The End Of Jobs. Now, he says he’s at a point where he can start companies and work with other entrepreneurs. For anyone that’s interested in reaching out to Jeff, you can do so by visiting www.jeffwald.com.

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The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/