Navigating Technology and the Future of Work with Jeff Wald

Corey Kupfer
4 min readFeb 22, 2023

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 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 toward a gig economy and its impact on workers, companies, and society.

Jeff’s expertise in the staffing industry has earned him recognition by Staffing Industry Analysts as one of the 100 Most Influential People in Staffing. He is a former officer in the Auxiliary Unit of the New York Police Department and a member of both the Young Presidents Organization (YPO) and MENSA.

Jeff Wald joins us on the DealQuest Podcast to share insights on the future of work and technology, including AI, automation, and the pandemic trend of hiring remote workers and working from home. Listen now:

RAISING CAPITAL IN THE 21ST CENTURY

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.

THE SOCIAL IMPACT OF THE EVOLUTION OF WORK

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.

The rapid pace of technological advancements and automation is changing the nature of work. The current landscape of the job market is a microcosm of the macro trend that is sweeping the world. The downside, however, is people working in certain industries risk losing their jobs due to automation and technological advancements. While it is true that on a macro level, the economy will continue to grow and the standard of living will rise, the same cannot be said for everyone. There will be job functions that will be lost forever, and this is a concern that cannot be ignored.

While the overall trend is positive, it is of little comfort to those who are negatively affected. This is why it is critical that we as a society do a better job of supporting those who are being left behind. To ensure success for all, society must invest in retraining and reskilling programs for those negatively impacted by changes in the job market. Providing support for these individuals leads to better outcomes and a more favorable return on investment compared to supporting them through disability, unemployment, or welfare programs.

TECHNOLOGY & INVESTING

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 toward 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.

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.

If you want to find out how deal-ready you are, take the Deal-Ready Assessment today!

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Corey Kupfer

Corey Kupfer is an expert strategist, negotiator and dealmaker with 35+ years of experience. He is also the creator and host of the DealQuest Podcast.