Knowledge comes with experience, and Jeff Leventhal has 25 years of experience in the tech startup world, including leading five companies from idea to exit and investing in many others. It’s an understatement to say he’s learned a few things on his entrepreneurial journey.

Leventhal’s great professional passion has been using technology to facilitate the delivery of professional services. His current iteration on solving this problem is WorkRails, a SaaS solution that helps other software companies sell and deliver their products. He’s also a Partner at BOLDstart Ventures, a “first check” investor for enterprise software founders.

Leventhal is great at telling engaging stories, and he transfers much of his wisdom through personal anecdotes. He shares some of his best tales in our interview, providing insights on acting in harmony with your internal wiring, socializing your business ideas and evaluating feedback, and building a team that will impress investors.

My thanks go out to Leventhal for letting me pick his brain and giving me with a few good laughs during our conversation. Check out Leventhal’s LinkedIn page to learn more about his long and impressive career, and have fun listening to this episode of Powderkeg: Igniting Startups.

In this episode with Jeff Leventhal, you’ll learn:

  • Why big career decisions often come down to your personal “wiring” (5:07)
  • A cheap, easy way to perform market research (11:12)
  • The six “value creation moments” of a startup (14:38)
  • How to win over VCs with the strength of your team (21:52)
  • High-level tips for socializing your ideas and receiving criticism (27:34)
  • Why New York City is a natural environment for entrepreneurs to flourish (33:44)

Please enjoy this conversation with Jeff Leventhal!

This episode of Powderkeg is brought to you by DeveloperTown. If you’re a business leader trying to turn a great idea into a product with traction, this is for you.

DeveloperTown works with clients ranging from entrepreneurs to Fortune 100 companies who want to build and launch an app or digital product. They’re able to take the process they use with early stage companies to help big companies move like a startup.

So if you have an idea for a web or mobile app, or need help identifying the great ideas within your company, go to

If you like this episode, please subscribe and leave us a review on iTunes. You can also follow us on Soundcloud or Stitcher. We have an incredible lineup of interviews we’ll be releasing every Tuesday here on the Powderkeg Podcast.

Jeff Leventhal Quotes from This Episode of Powderkeg:

“Closing doors may force you to leverage skills inside you that you didn’t even know you had.” — Jeff Leventhal

“When you’re doing a startup, nobody wants to hear from you. Be prepared for people to tell you your idea sucks.” — Jeff Leventhal

“I look at my business plan as a work of art. The same way a musician looks at a song, or an artist looks at a canvas, my business plan is my canvas, and there’s vulnerability when you show it to somebody.” — Jeff Leventhal

“Entrepreneurship is not a career choice. It chooses you. It chose me, and I’ve done it, and it’s hard.” — Jeff Leventhal

Links and Resources Mentioned in this Episode:

Companies and Organizations:

Information Builders



VC Firms:

BOLDstart Ventures


Coworking Spaces:


Software and Apps:



Cornell University

Stanford University

Trade Shows:

PC Expo


Jonathan Lehr

Jeff Bezos

Did you enjoy this conversation? Thank Jeff on Twitter!

If you enjoyed this session and have 3 seconds to spare, let Jeff Leventhal know via Twitter by clicking on the link below:

Click here to say hi and thank Jeff on twitter!


What stood out most to you about what Jeff shares in this podcast?

For me, it’s why big career decisions often come down to your personal “wiring”.

You? Leave a comment below.


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