RS289: Where Branding Goes Wrong with Ruben Gamez

Rogue Startups
Rogue Startups
RS289: Where Branding Goes Wrong with Ruben Gamez

On this episode of Rogue Startups, Craig chats with Ruben Gamez, the founder of Bidsketch and SignWell. Ruben shares his opinions and tips about various marketing strategies, branding, and growth. In addition to talking about the podcasting industry and Castos, Craig and Ruben also dive into how to proactively find deals and connect with customers.

Originally a software developer, Ruben bootstrapped Bidsketch while working full-time and was quickly able to grow it into a profitable business. He spent several years working for a billion-dollar payroll company. There he helped build and manage a custom proposal system that was used to regularly win seven and eight-figure deals. When he saw there was a need for an alternative to the hard-to-use and expensive e-signature software already out there, he decided to start SignWell in order to simplify how documents get signed for millions of people and businesses.

Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at And as always, if you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week!


  • Inbound volume: proactively finding bigger deals
  • Getting in front of customers who have problems you can solve
  • Objectively looking at how much room is in your market
  • Ad-tech in the podcasting industry
  • Approaching growth from different perspectives
  • Ruben’s thoughts on building a brand and how branding works
  • Burn rate and thinking ahead before you tap out 


Ruben on Twitter/X




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