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How to Start Multiple Businesses, Blaze Your Own Path, and Instigate like a Professional: an Interview with Clay Hebert

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In the Trenches: Episode 2Spindows

Here is the 2nd episode of “In the Trenches: The Resistance Broadcast Interview Series” and today I had the honor of interviewing Clay Hebert.

[Listen to the Interview by clicking this link]

Clay is an entrepreneur, blogger, multitasking ninja, and all around instigator.

Clay began his career at Accenture.  After ten years at Accenture, Clay left corporate America and got his MBA from Seth Godin.

Currently, Clay is building Spindows.com, a new startup that will change the way organizations collaborate (think of it like speed dating + skype + your organization).

Clay has created a number of startups, including:  Tribes Win, a marketing strategy and innovation agency, where he helped brands lead their tribes.  More recently, Clay began a new project called Work Hacks, where he helps people live a more productive, efficient, and streamlined lifestyle.

You can read Clay’s blog and find out more about him at Daily Sense.

Clay is a sought after speaker, writer, and entrepreneur, and this interview is essential listening for anyone looking to start their own project (book, business, or blog).

In the Trenches: an Interview with Clay Hebert – How to Start Multiple Businesses, Blaze Your Own Path, and Instigate like a Professional

In this interview, we cover:

  • Why it’s hard to be a linchpin inside a large, bureaucratic organization
  • What it was like to transition to Seth Godin’s MBA program
  • Why making a slower transition from conventional work to entrepreneurship might be the right strategy for many people
  • Why entrepreneurship isn’t jumping off a building and hoping the parachute deploys (it’s less risky if you do it right)
  • How you don’t have to quit your day job to make it as an entrepreneur
  • The difference between a freelancer and an entrepreneur; between a business that can’t scale and one that can
  • Why online software is such a compelling proposition for entrepreneurs (and how to make it actually work)
  • And one extremely compelling piece of advice for aspiring entrepreneurs
  • Why it’s essential you validate your ideas before you jump into your next project
  • Why you don’t need to raise tons of capital to create a successful startup from scratch

You can read more about Tribes Win here, Work Hacks here, and read Clay’s blog here.

Be sure to check out Spindows here, and read up on some of the interviews Clay has done regarding the new platform he is developing (very interesting stuff).

If you liked this interview, share it with everyone you know and reach out to Clay and thank him!


Some other highlights from our conversation:

Purple Cow: The essential guide on marketing and creating remarkable products.

War: A nonfiction work that follows a group of soldiers in Afghanistan – not for the feint of heart.

Crush It!: If you want to dominate in the online arena, you need to leverage the connection economy.

The Lean Startup: An incredible book on the power of validating an idea before you begin, failing fast and scaling fast (with minimal resources – great for the solopreneur).

Launchrock: Starting a project?  Validate it first.

Skillshare: Have something worth teaching?  Make money sharing your knowledge!


If you haven’t had a chance, catch In the Trenches: Episode 1 here.


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