Episode 224: Navigating Technology and the Future of Work with Jeff Wald

Season #1

Jeff Wald is a serial entrepreneur, author, speaker, investor, and board member. He co-founded Work Market, which was acquired by ADP in 2018, and founded Spinback, which was purchased by Salesforce.com. He has served on various boards and is an adviser to companies and organizations, including the X-Prize’s Rapid Reskilling Initiative. He is the author of the Amazon best-seller, The End of Jobs: The Rise of On-Demand Workers and Agile Corporations. The End Of Jobs explores the shift towards a gig economy and its impact on workers, companies, and society.



The process of raising capital for a startup is a crucial part of its journey. In order to secure the right funding, it is important to approach the right investors who are interested in investing in your company. Jeff suggests avoiding cold emails as they are no longer effective, with him personally responding to none of them. Instead, Jeff suggests using platforms like LinkedIn to connect with potential investors through mutual friends or colleagues, which increases the chances of making a personal connection and securing funding.


As Jeff says, "Money comes with people attached,” and it's important to know their expectations. Having the right capital partner is essential, as they are part of the company's management team and have a say in its direction. If the right partner isn't found, it's better to slow growth or explore other alternatives rather than take on a bad partner that could harm the company's future. Slow growth may not be ideal, but it's preferable to a bad partner.



Jeff's book, The End of Jobs: The Rise of On-Demand Workers and Agile Corporations, is a reflection of his belief that people tend to romanticize the past, complain about the present, and fear the future. He wants to help people understand that work has continually gotten better over time and that this trend will likely continue in the future. He believes that by focusing on the future of work, we can prepare ourselves for the changes that are sure to come and make the most of the opportunities that will arise.



As an angel investor, Jeff has learned some important lessons about investing and the future of work. He believes that his ability to invest wisely is limited by the amount of time he has available, so he has shifted his focus towards becoming a Limited Partner in venture funds. This allows him to deploy capital to venture funds with a specific focus, such as cybersecurity, marijuana, enterprise software, or the future of work.


Technology is, once again, a driving force of change in the world of investing. Companies are always making big investment decisions, and as technology continues to advance, the gap between what can be built and what has been built will increase. Jeff believes that this shift will drive companies to adapt and make changes, which will ultimately lead to progress.




Purchase The End of Jobs: The Rise of On-Demand Workers and Agile Corporations

Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.

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