Behind the Scenes – A Founder’s Lessons from Selling 4 Businesses

About the Episode

Jeff Wald joins us to talk extensively about his experience buying and selling companies. Jeff shares his insights into buying versus building a business, learning from your mistakes, how long the process can take, and building a company to sell later for a massive profit. His experience starting and selling his technology companies will give you invaluable insights as he discusses this process and offers advice. Jeff is also the author of two books and is a frequent speaker on the topics of startups and labor issues.

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In this Episode

2:15 What did you learn from your first big failure?
6:30 What did you do differently with your second company?
7:40 How long did it take from start to exit?
8:30 How long did the transaction take?
9:00 What was your role in the negotiations and what did you learn?
11:05 How hard would it be to build a company and sell it in two years for tens of millions of dollars?
24:30 The buy vs. build decision — it is now becoming cheaper to build.
28:00 How did selling both of your businesses impact your life?
29:30 How did your mindset change after you sold your business?
34:20 What really makes you happy now that you have all of your financial needs met?
41:00 How do you spend your time now? What are your goals?
50:30 What is your advice to business owners?


  • You learn more from your failures than from your successes.
  • Money comes with people and expectations attached.

Resources Mentioned in This Episode

Meet Our Guest

Jeff Wald

Jeff Wald

Founder of WorkMarket

Jeff Wald is the Founder of WorkMarket, an enterprise software platform that enables companies to manage freelancers, which he sold to ADP. Jeff has founded several technology companies, including Spinback, a social sharing platform (eventually purchased by Jeff began his career in finance, serving as Managing Director at activist hedge fund Barington Capital Group, as a Vice President at venture capital firm GlenRock, and various roles in the M&A Group at JP Morgan. Jeff is an active angel investor and startup advisor, as well as serving on numerous public and private Boards of Directors. He also formerly served as an officer in the Auxiliary Unit of the New York Police Department. Jeff is the author of The Birthday Rules and The End of Jobs: The Rise of On-Demand Workers and Agile Corporations. Jeff frequently speaks at conferences and in the media on startups and labor issues. Jeff holds an MBA from Harvard University and an MS and BS from Cornell University.

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