Fail...Fail...Win...Fail...Win...Watch Me Win Big! Meet Eli Rubel.

Overcoming Imposter Syndrome: Pushing Through the Hard Days

About Eli Rubel

  • Started and sold two companies

  • Runs two bootstrapped B2B agencies (marketing / design) that have produced $9.8M in profit since 2020 while working 25h/wk

  • He's building a new agency completely in the open (sharing all profit metrics etc) 

  • #81 on the Inc5000

Sound Bites

I wanted to pick the most boring corner of the software world that I could so I wouldn't be competing with a bunch of really smart people."

Eli Rubel on The Sales Podcast
  • "If you can work in the service industry at any point in your career, you learn so many life skills in such a condensed period of time."

  • "There needs to be that counterbalance dose of honesty and accuracy."

I can help a whole lot of people because I'm not doing everything for them."

Wes Schaeffer with Eli Rubel on The Sales Podcast


  • 00:00 Introduction and Background

  • 02:00 Starting and Selling Companies

  • 07:03 Discovering the Boring Side of Software

  • 09:09 Acquiring and Turning Around an E-commerce Company

  • 20:00 Overcoming Imposter Syndrome

  • 24:25 From Zero to Six: The Value of Incremental Progress

  • 28:23 Getting into the Nitty-Gritty: The Importance of Doing the Boring Tasks

  • 33:48 Building a Million-Dollar Business: Taking the Audience Along for the Ride

  • 36:29 The Power of a Virtual Assistant: Outsourcing to Maximize Efficiency

  • 43:48 Headsets and Mountain Biking: A Lighthearted Conclusion


  • Success in entrepreneurship requires discipline, perseverance, and the ability to learn from failures.

  • Pivoting and adapting to market needs is crucial for the growth and success of a business.

  • Transparency and open communication are essential in building trust with customers and employees.

  • Imposter syndrome is common among entrepreneurs, but pushing through the hard days is what separates successful entrepreneurs from others. Focus on small, incremental steps to build a business from scratch

  • Provide just enough help to overcome obstacles

  • Be willing to do the boring tasks that are necessary for success

  • Hire a virtual assistant to free up time for strategic work

  • Outsource tasks to maximize efficiency

  • Enjoy the journey and celebrate milestones along the way

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