84: How to Build a Successful Business without Startup Funding with Rob Walling of Drip

The Foundr Podcast with Nathan Chan

As a full time software developer working for a large company, Rob Walling dreamt of becoming an entrepreneur – and more than a decade later he has obtained serial entrepreneur status.

Rob Walling is many things…as a serial entrepreneur he has been at the helm of several tech companies including Drip, Micropreneur, HitTail and DotNetNovice. His personal brand is supported by regular posts to his blog which he forayed into a book, Start Small and Stay Small: A Developer’s Guide to Launching a Startup. In his spare time, he wears the hat of a podcaster, conference host, teacher, angel investor and audio book junkie.

When the entrepreneurial itch first infiltrated Rob’s being, he left his full time job and began consulting and freelancing. The move was great at first but he soon found that freelancing and consulting was a lot like working for someone else – which was seriously uncool.

His new dream was products – build something that people will buy on his own terms without the watchful gaze of a boss. But, it didn’t work like that…instead; Rob’s second transition came when he acquired a small software application and tasted true freedom. As Rob puts it, “My goal was to cobble together enough of a portfolio so that I could stop consulting.”

His acquisitions ran the gamut from a site that sold beach towels (but ranked high on Google) to a book on bonsai trees but eventually, he was able to give up consulting completely. He developed a strategy built on incremental progress - a solid stair stepping approach that has made every acquisition, his biggest acquisition.

In this interview you will learn:

• What to do when you want to bootstrap and how to make it work
• The secrets to keeping yourself in check and managing expectations
• The secrets to self-confidence in the startup world
• How to build yourself a top mastermind group
• What it takes to ensure that you have a proven product that people will love
• & much more!