Bringing Back Jeff Wald To Discuss The End Of Jobs

Our next guest is so amazing, we had to interview him a second time! He was on nearly 5 years ago on Episode 8! Jeff Wald is an entrepreneur who has started three technology companies, with his latest company, WorkMarket, being sold to ADP.

Jeff Wald | Author | The End of Jobs

Jeff Wald | Author | The End of Jobs

Our next guest is so amazing, we had to interview him a second time! Jeff Wald was on Ambition Today nearly 5 years ago on Episode 8 and we are bringing him back for episode 62!

Jeff Wald is an entrepreneur who has started three technology companies, and since we last spoke with Jeff, he sold his latest company, WorkMarket, to ADP. Jeff is also a Board Member on the following boards: Steel Connect, Costar Technologies, TransfrVR, Peerless Systems, and Register.com. During this episode we catch up with Jeff and talk about his new book, “The End of Jobs: The Rise of On-Demand Workers and Agile Corporations”. Tune in to hear all about his book as well as statistics regarding the workforce in 2020:

Topics Discussed:

  • His experience selling the company.

  • The impact of remote working.

  • How to create “social squads” in your company.

  • The importance of defining the goal of any meeting.

  • The steps of technological change, mechanization, electrification, computerization and what comes next with robots and AI.

Quote of the Episode:

“Every time {we revolutionize} we ended up with more jobs, at a higher standard of living, with working fewer hours, that is definitively clear through history.” - Jeff Wald

The Greatest Piece of Advice:
Checkout the podcast’s back channel, The A-List where you can listen to exclusive audio clips containing the single greatest piece of advice our guests have ever learned!


Links & show notes from this episode:


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Ambition Today: Jeff Wald, Co-founder of Work Market, talks Harvard, NYPD, Venture Capital, Startups, and Mentoring

On episode eight Jeff Wald, Co-founder and President of Work Market and his incredibly charitable no shave Movember mustache join Ambition Today. "The only thing I know with 100% certainty is that it ain't going down like this." - Jeff Wald

Jeff Wald, Work Market

Jeff Wald, Work Market

On episode eight Jeff Wald, Co-founder and President of Work Market join's Ambition Today. 

"The only thing I know with 100% certainty is that it ain't going down like this." - Jeff Wald

Jeff Wald’s background is nothing short of impressive. He started at Cornell University and then went to J.P. Morgan. He then went back to school at Harvard for an MBA. After Harvard Jeff spent time at Glen Rock Group before going on to Co-found Spin Back. The wild ride of Spinback, his first startup, took Jeff to almost moving back home after coming close to running out of money. The answer was to rebuild the business which later ended up getting acquired. After acquisition Jeff went to Barington Capital Group, and finally to his current company where he is the Co-founder and President of Work Market. Did I mention he was also an auxiliary member of the NYPD as well? This is an episode packed full of insights: 

  • Is getting a Master's of Business Administration worth the return on investment?

  • Should you start a company or get an MBA?

  • The value of spending time with Entrepreneurs.

  • How to break into Venture Capital.

  • Leaving a job in Venture Capital to start a new company.

  • How to attract high quality investors in your startups such as Fred Wilson from Union Square Ventures, Spark Capital, and Softbank.

  • The one question you should start every meeting with.

  • The four different types of conversations.

  • Differences between Advisors and Mentors.

  • The importance of giving back to others

The Ambition Today Question of the Day:

Who would win in a fight, Batman vs Superman?

Be sure to listen and subscribe to Ambition Today in the iTunes Store for iOS and on Stitcher for Android


Links from this episode: 

Who should I interview next?  Please let me know on Twitter or in the comments. Do you enjoy this podcast? If so, please leave a short review in the comments below.  It keeps me going…

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Founder Institute, Entrepreneurship, Mentors, Team Kevin Siskar Founder Institute, Entrepreneurship, Mentors, Team Kevin Siskar

Why I Mentor by Jeff Wald

This is a guest post from Founder Institute New York Mentor Jeff Wald titled "Why I Mentor" as was originally published in Huffington Post. Jeff has asked me to share the post and it contains some incredibly valuable insight on the Mentor / Mentee relationship.

Jeff Wald

Jeff Wald

This is a guest post from Founder Institute New York mentor Jeff Wald titled "Why I Mentor" as was originally published in Huffington Post. Jeff has asked me to share the post and it contains some incredibly valuable insight on the Mentor / Mentee relationship. My favorite quote from it is: 

"I believe we have an obligation to help fellow travelers."

Jeff Wald is Co-Founder and President of Work Market, the leading enterprise-class platform for the management of contract and freelance talent. Jeff has a long track record as a successful entrepreneur across the technology and services landscape. He has successfully built and sold multiple tech companies, including SpinBack to Buddy Media, which was subsequently purchased by Salesforce.com for $800 million.  


Why I Mentor

by Jeff Wald

A startup founder recently asked me a simple, yet startling, question during our monthly meetings. We have been working together for nearly two years, and as with all startups she has had her ups and downs. We have had all manner of conversations over the years and yet, in this one instance, her simple question floored me - "When I asked if you would be my mentor, why did you say yes?"

The first thing that surprised me was that she said "mentor" and not "adviser". I have the pleasure of advising many companies. This means that I meet with them every now and again to offer some thoughts on a discrete problem, or I make an introduction or two. However, my relationship here was different. I was more than an adviser. I was a mentor to her. We meet once a month and I know a tremendous amount about her business, where she has been and where she hopes to go. I am proud to be her mentor so I wanted to provide an honest answer.

After collecting myself, I explained that there were three reasons why I said yes‎, in no particular order of importance:

  • She was the first to ask.
  • Mentoring helps reinforce the lessons I'm learning at my own company.
  • I believe we have an obligation to help fellow travelers.

‎She was the first to ask. She and I met at The Founders Institute (FI), an organization where I have been teaching for some years. The FI is the world's largest entrepreneur training and startup launch program with chapters across 50 countries. In each chapter "experienced" founders teach a series of classes to aspiring founders.

Many of the students I have taught over the years will email and ask if they can discuss their businesses. I am always happy to help, so‎ I'll meet with them and offer candid feedback on their ideas. These aspiring founders frequently end our time together by asking to return when their plans have progressed. I would always say yes, but few have ever returned. Some never make any progress; some don't like the very direct feedback I am prone to give; some presumably just forget to follow up. So when asked why I agreed to mentor her, part of the answer was simply that she asked. I had time and she asked, so I said yes. If someone had asked before her, then I really would not have had the time.

Mentoring helps reinforce the lessons I am learning at my own company. I have learned a great many things on my entrepreneurial journey at Work Market: mistakes I hopefully won't repeat, important lessons to refer back to and valuable insights from colleagues. Mentoring this founder and hearing about her own struggles and breakthroughs has forced me to reflect on when we were at a similar stage as a company. Offering her advice and describing the opportunities we missed (we all miss many) helps to codify these hard-won lessons and prepares me for my next adventure.

We have an obligation to help fellow travelers. I have walked this tumultuous, crazy, startup path three times. It's one of the hardest ‎journeys you will ever take. It will test limits you never knew you had and then demand you to push beyond them. So, when the journey ends, regardless of the outcome, you have gained invaluable experience. Pass it along. I can promise you this: whatever outcome you had, you didn't get there alone. You had co-founders, colleagues, investors, mentors, advisers, customers, and of course friends and family that all helped in sometimes small, but many times, immeasurable ways. You owe it to them, as well as to yourself, to help others who are embarking upon that similar difficult path. No one can make it alone.

If you have made it to the end of a startup journey, and if you have the time, stretch out your hand and help the next traveler. They will be grateful and you will greatly benefit as well.

And in the meantime, check out what Beatriz and her team at DADA have built.

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